Category: 108-37-2

Some common heterocyclic compound, 108-37-2, name is 1-Bromo-3-chlorobenzene, molecular formula is C6H4BrCl, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Quality Control of 1-Bromo-3-chlorobenzene

To a stirred solution of 1-bromo-3-chlorobenzene (1.0 g, 5.22 mmol, 1.00 equiv) in tetrahydrofuran (5 mL), was added4,4,5 ,5-tetramethyl-2- (tetramethyl- 1 ,3,2-dioxaborolan-2-yl)- 1,3 ,2-dioxaborolane (800 mg, 3.15mmol, 0.60 equiv), 4-tert-butyl-2-(4-tert-butylpyridin-2-yl)pyridine (43 mg, 0.16 mmol, 0.03 equiv), bis(( 1Z,5Z)-cycloocta- 1 ,5-diene)dimethyl-2,4-dioxa- 1 ,3-diiridabicyclo[ 1.1 .0]butane-2,4-diium- 1 ,3-diuide (33 mg, 0.05 mmol, 0.01 equiv) under nitrogen. The mixture was stuffed for overnight at 80 C. The solid was filtered out and the filtrate was concentrated under vacuum. Crude product was purified by a silica gelcolumn with ethyl acetate/petroleum ether (1:10) to give 1.29 g (78%) of the title compound as colorless oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 108-37-2, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; BLAQUIERE, Nicole; BURCH, Jason; CASTANEDO, Georgette; FENG, Jianwen A.; HU, Baihua; STABEN, Steven; WU, Guosheng; YUEN, Po-wai; WO2015/25025; (2015); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 108-37-2, name is 1-Bromo-3-chlorobenzene, molecular formula is C6H4BrCl, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. name: 1-Bromo-3-chlorobenzene

General procedure: To a round-bottom flask equipped with a magnetic stirring bar were added monomeric palladacycle 2 (0.4 mol %), K2CO3 (1.1 mmol), olefin (2.2 mmol) and aryl halide (1 mmol) in NMP (3 mL). The mixture was heated at 130 C using an oil bath and the progress was monitored by TLC (hexane/EtOAc, 80:20) and gas chromatography (GC). After completing the reaction, the mixture was diluted with n-hexane (30 mL) and H2O. The organic layer was washed with brine (20 mL), dried over Na2SO4, and concentrated under reduced pressure. The residue was purified by recrystallization from EtOH and H2O. The products were characterized by comparing their mp and IR, 1H and 13C NMR spectra with those reported in the literature.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 108-37-2, its application will become more common.

Reference:
Article; Hajipour, Abdol Reza; Rafiee, Fatemeh; Rouho, Arnold E.; Tetrahedron Letters; vol. 52; 37; (2011); p. 4782 – 4787;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 108-37-2, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 108-37-2, name is 1-Bromo-3-chlorobenzene, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of diisopropylamine (76 niL, 0.4 mol) in anhydrous THF (664 rnL) and n-hexane (220 rnL) was added 2.5 M n-BuLi (160 rnL, 0.4 mol) dropwise at -78 0C over 1 h. The mixture was stirred for 1 h at -78 0C and a solution of 1-bromo- 3-chlorobenzene (76 g, 0.4 mol) in anhydrous THF (300 mL) was added dropwise at – 78 0C. After stirring for an additional 1 h at the same temperature, a solution of iodine (101 g, 0.4 mol) in anhydrous THF (400 mL) was added dropwise at -78 0C. The temperature was raised from -78 0C to rt during 2 h. After stirring for 18 h at rt, the mixture was concentrated in vacuo to give the crude product (120 g) which was distilled under reduced pressure to give l-bromo-3-fluoro-2-iodobenzene (115 g, 91%). 1H NMR (400MHz, CDCl3): 7.12-7.18 (t, IH), 7.35-7.41 (dd, IH), 7.49-7.54 (dd, IH); MS (E/Z): 317 (M+H+)

The chemical industry reduces the impact on the environment during synthesis 1-Bromo-3-chlorobenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; VITAE PHARMACEUTICALS, INC.; WO2008/124577; (2008); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 108-37-2, name is 1-Bromo-3-chlorobenzene, This compound has unique chemical properties. The synthetic route is as follows., Safety of 1-Bromo-3-chlorobenzene

General procedure: In a round-bottom flask equipped with a magnetic stirring bar to a mixture of K2CO3 (1.1 mmol), olefin (2.2 mmol) and aryl halide (1 mmol) in NMP (3 ml) were added 0.1 mol% of palladacycle complex (A) and equipped with a condenser for refluxing. The above mixture was heated at 130 C in an oil bath. The reaction’s progress was monitored by TLC (hexane/EtOAc, 80:20) and gas chromatography (GC). After completion of the reaction the mixturewas diluted with n-hexane and water. The organic layer was washed with brine, dried over Na2SO4, and concentrated under reduced pressure. The residue was purified by recrystallization from ethanol and water. The products were characterized by comparing their m.p., IR, 1H, 13C NMR spectra with those found in the literature [41-43].

According to the analysis of related databases, 108-37-2, the application of this compound in the production field has become more and more popular.

Reference:
Short Survey; Hajipour, Abdol R.; Rafiee, Fatemeh; Journal of Organometallic Chemistry; vol. 696; 13; (2011); p. 2669 – 2675;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

108-37-2, These common heterocyclic compound, 108-37-2, name is 1-Bromo-3-chlorobenzene, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Under a nitrogen atmosphere, a 5 L dry and clean four-neck round bottom flask was charged with diisopropylamine (72.8 g, 0.72 mol, 1.06 eq) and 1500 mL of anhydrous tetrahydrofuran, and the temperature was reduced to -70 C.Add n-butyllithium solution (272mL, 2.5M, 0.68mol, 1.0eq), stir to cool to -70 , slowly add D-1 (130g, 0.68mol, 1.0eq) dropwise, and maintain the reaction for 1h after the addition.Slowly add iodine-tetrahydrofuran solution (172g iodine / 300ml THF, 0.68mol, 1.0eq),After the addition, the reaction was maintained for 1 h.The temperature was slowly raised to room temperature, and the reaction was monitored by HPLC for completion.The reaction was quenched with 500 mL of 5% Na2S2O3 solution, and extracted with 2 L of methyl tert-butyl ether.The organic phase was washed with 1500 mL of saturated saline and dried over anhydrous sodium sulfate.Concentrated under reduced pressure to obtain an oil, and recrystallized by adding 600 mL of ethanol.184 g (F-1) of white flaky solid was obtained by filtration,The yield was 85%.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 108-37-2.

Reference:
Patent; Ningbo Lumilan New Materials Co., Ltd.; Ningbo Dinghao Optoelectric Materials Technology Co., Ltd.; Zhang Yuxiang; Zhang Qingyun; Ding Huanda; Chen Zhikuan; (41 pag.)CN110551154; (2019); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

108-37-2, A common compound: 108-37-2, name is 1-Bromo-3-chlorobenzene, belongs to chlorides-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

General procedure: A mixture of aryl halide (1 mmol), phenyltributyltin (1.2 mmol), K2CO3 (1 mmol), and ortho-palladated catalyst (0.3 mol %) in DMF (2 mL) in a round-bottom flask equipped with a condenser was placed into a Milestone microwave reactor. Initially using a microwave power of 500 W, the temperature was ramped from room temperature to 90 C, (ca. 1 min), and then held at this temperature until the reaction was complete. During this time, the power was modulated automatically to keep the reaction mixture at 90 C. The mixture was stirred continuously using an appropriate magnet during the reaction. After the reaction was complete, the mixture was cooled to room temperature and diluted with H2O (30 ml) and Et2O (30 ml). The organic phase was washed with saturated KF solution (30 ml), and dried over MgSO4. The solution was filtered and the solvent evaporated using a rotary evaporator. The residue was purified by silica gel column chromatography [n-hexane or n-hexane/EtOAc (9:1)].

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 1-Bromo-3-chlorobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Hajipour, Abdol Reza; Rafiee, Fatemeh; Tetrahedron Letters; vol. 53; 35; (2012); p. 4661 – 4664;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

108-37-2, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 108-37-2 name is 1-Bromo-3-chlorobenzene, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

0.72 g (29.6 mmol) of magnesium dust was immersed in 15 mL of anhydrous tetrahydrofuran, and one iodine was added thereto, and two drops of m-chlorobromobenzene were added dropwise at room temperature. The turbidity was changed by the air gun micro-heating system, and the system was slightly boiled and dropped into 15 mL of tetrahydrofuran and 5.61 g.A mixture of (29.3 mmol) m-bromochlorobenzene was heated and refluxed for 3 hours after the dropwise addition. Decrease to room temperature and use until the next step. To a solution of the format reagent in tetrahydrofuran, 0.34 g (1.8 mmol) of cuprous iodide was added, and the mixture was stirred at room temperature for 1 hour. Slowly drip propargyl alcohol0.66 g (11.7 mmol), after completion of the dropwise addition, was heated to reflux for 24 hours. After cooling, a saturated ammonium chloride solution was added dropwise to adjust pH = 5. Extracted 3 times with 30 mL of ethyl acetate, combined organic phase, washed with saturated sodium hydrogen carbonate solution, washed with saturated sodium chloride solution, anhydrousDry over sodium sulfate. After spin-drying, 10 mL of methanol was added to the system to precipitate a solid, and the solid was taken out and distilled under reduced pressure to give 1.84 g of a pale yellow oily liquid. The yield was 92.3%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-3-chlorobenzene, and friends who are interested can also refer to it.

Reference:
Patent; Hebei University of Science and Technology; Zhang Guogang; Du Wei; Zhao Yanli; Feng Xue; Song Miaomiao; Song Wei; Yang Ying; (11 pag.)CN108484535; (2018); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

108-37-2, A common compound: 108-37-2, name is 1-Bromo-3-chlorobenzene, belongs to chlorides-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

General procedure: To a round-bottom flask equipped with a magnetic stirring bar were added monomeric palladacycle 2 (0.4 mol %), K2CO3 (1.1 mmol), olefin (2.2 mmol) and aryl halide (1 mmol) in NMP (3 mL). The mixture was heated at 130 C using an oil bath and the progress was monitored by TLC (hexane/EtOAc, 80:20) and gas chromatography (GC). After completing the reaction, the mixture was diluted with n-hexane (30 mL) and H2O. The organic layer was washed with brine (20 mL), dried over Na2SO4, and concentrated under reduced pressure. The residue was purified by recrystallization from EtOH and H2O. The products were characterized by comparing their mp and IR, 1H and 13C NMR spectra with those reported in the literature.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 1-Bromo-3-chlorobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Hajipour, Abdol Reza; Rafiee, Fatemeh; Rouho, Arnold E.; Tetrahedron Letters; vol. 52; 37; (2011); p. 4782 – 4787;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

108-37-2, These common heterocyclic compound, 108-37-2, name is 1-Bromo-3-chlorobenzene, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

A mixture of 10(a) (prepared similarly to Example 9A, step 1, using appropriate starting material, 460 mg, 1.00 mmol), diboron pinacol ester (305 mg, 1.20 mmol), potassium acetate (294 mg, 3.00 mmol), 1,1′-bis(diphenylphosphino)ferrocene (55 mg, 0.10 mmol), and dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane adduct (82 mg, 0.10 mmol) in 1,4-dioxane (5 mL) was heated in a closed pressure tube under N2 at 80 C for 2 h. The mixture was cooled to room temperature. To this mixture was added 1-bromo-3-chloro-benzene (235 muL, 2.00 mmol), K3PO4 (636 mg, 3.00 mmol), dichloro-[1,1′-bis(diphenylphosphino)ferrocene]-palladium (II) dichloromethane adduct (41 mg, 0.050 mmol), and 1,4-dioxane (5 mL). The mixture was heated in a closed pressure tube under nitrogen at 80 C for 16 h. The mixture was partitioned between NH4Cl (saturated) and EtOAc. The organic layer was washed with brine, dried (MgSO4), and concentrated in vacuo. Flash chromatography of the residue on a silica gel column with EtOAc:hexane (20:80, then 25:75) as eluent gave (+)-Example 10 (360 mg, 85%) as off-white solids. HCl salt: off-white solids; MS (FAB) m/z 422 (MH+, 100).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 108-37-2.

Reference:
Patent; SCHERING CORPORATION; EP1036072; (2004); B1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

A common compound: 108-37-2, name is 1-Bromo-3-chlorobenzene, belongs to chlorides-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 108-37-2

(Setting-Up and Reaction) To a 50 mL two-necked round-bottomed flask, [PdCl (pi-allyl) ]2 (10.8 mg, 0. 05 mol%) and cBRIDP (41.8 mg, 0.2 mol%) were added. A three-way stopcock was attached to the flask, and the inside was purged with nitrogen. Subsequently, anhydrous THF (5 mL) was added, and the mixture was shaken at room temperature for 1 minute and further diluted with anhydrous xylenes (20 mL) to prepare a catalyst solution (25 mL). On the other hand, to a 300 mL four-necked round-bottomed flask, a three-way stopcock, a Teflon-coated magnetic stirring bar, a condenser, a 50 mL dropping funnel, and a thermometer were attached, and the inside was purged with nitrogen. To this flask, carbazole (20.4 g, 178.8mmol, 1.03eq.), anhydrous xylenes (100 mL), and anhydrous THF (10 mL) were sequentially added, and the obtained reactant suspension was cooled to 5C by use of an ice-water bath. Subsequently, a MeMgCl/THF solution (3.02 mol/L, 40.0 mL, 120.8 mmol, 1.02 eq.) was placed in the dropping funnel, and added dropwise over 20 minutes, while the reactant suspension was being stirred, and the inside temperature was being kept at 20C or below. Then, the dropping funnel was rinsed with anhydrous xylenes (20 mL). Subsequently, 3-bromochlorobenzene (14.0 mL, 118.4 mmol, 1.0 eq.) and the catalyst solution (25 mL) were sequentially added to the reaction solution, and then the mixture was stirred for 1 hour under reflux (approximately 110C). Reaction Conversion: >99.9% (GC). (Post Treatment) After the obtained suspension had been cooled to room temperature, water (60 mL) and ammonium chloride (3.2 g, approximately 0.5 eq.) were added. The mixture was filtered by use of diatomaceous earth, the aqueous layer was separated (Aqueous Layer 1: pH=9), and further the organic layer was washed with water (60 mL) (Aqueous Layer 2: pH=7). The organic layer was concentrated under reduced pressure, and the obtained brown viscous liquid was purified by silica gel column chromatography (Eluent: n-hexane/toluene=4/1 to 2/1) to give 32.4 g of title compound (8) as a colorless viscous liquid. Isolated Yield: 98.5%. For exact measurement of the weight, a toluene solution of title compound (8) (25% by weight, 0.900 mmol/g) was prepared after the purification and used in the second step. 1H NMR (300 MHz, CDCl3): delta=8.13 (dt, J=7.5, 0.9 Hz, 2H), 7.58 (t, J=2.1 Hz, 1H), 7.56-7.38 (m, 8H), 7.35-7.25 (m, 2H). 13C NMR (75 MHz, CDCl3): delta=140.5, 140.0, 135.4, 130.8, 127.6, 127.2, 126.1, 125.2, 123.5, 120.4, 120.3, 109.6.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 108-37-2, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Takasago International Corporation; Nakayama, Yuji; Yokoyama, Naota; EP2937355; (2015); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics