Category: 1996-30-1

Electric Literature of 1996-30-1, 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. 1996-30-1 name is 3-Bromo-4-fluorochlorobenzene, 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.

General procedure: 1.00 mmol arylhalide, 1.30 mmol furfural-boronic acid and 0.05 mmolBis(triphenylphosphine)palladium(II) dichloride were treated with 0.30 mLdimethoxyethane, 0.50 mL ethanol and 0.30 mL aqueous 2M sodium carbonate solution.The reaction was heated to 65C for 1h or until the TLC showed no remaining startingmaterial. The mixture was evaporated and extracted three times with ethyl acetate. Thecombined organic layers were washed with brine, dried over MgSO4, filtered andconcentrated. The crude product was purified by column chromatography usinghexanes/ethyl acetate (9:1).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Bromo-4-fluorochlorobenzene, and friends who are interested can also refer to it.

Reference:
Article; Krake, Susann H.; Martinez, Pablo David G.; McLaren, Jenna; Ryan, Eileen; Chen, Gong; White, Karen; Charman, Susan A.; Campbell, Simon; Willis, Paul; Dias, Luiz Carlos; European Journal of Medicinal Chemistry; vol. 126; (2017); p. 929 – 936;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 1996-30-1, name is 3-Bromo-4-fluorochlorobenzene, A new synthetic method of this compound is introduced below., Product Details of 1996-30-1

2-Fluoro-5-chlorobromobenzene 18a (11.0 g, 52.8 mmol), ethynyltrimethylsilane (7.7 g, 79 mmol) and triethylamine (60 mL) were mixed together, and then cuprous iodide (100 mg, 0.53 mmol) and ditriphenylphosphine palladium chloride (1.86 g, 2.65 mmol) were added, the reaction mixture was heated to 80 C. under a nitrogen atmosphere and stirring was continued for 4 hours, after the reaction was completed, the solvent was removed from the solution under reduced pressure, the residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate=100/1), so as to obtain the title product ((2-fluoro-5-chlorophenyl)ethynyl)trimethylsilane 18b (11.0 g, yellow oily substance), and the yield was 90%. 1H NMR (400 MHz, CDCl3) delta 7.45 (dd, J=6.0, 2.7 Hz, 1H), 7.28-7.22 (m, 1H), 7.02 (t, J=8.8 Hz, 1H), 0.29 (s, 9H).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; BEIJING INNOCARE PHARMA TECH CO., LTD.; Chen, Xiangyang; Gao, Yingxiang; Kong, Norman Xianglong; (59 pag.)US2019/210997; (2019); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 1996-30-1, name is 3-Bromo-4-fluorochlorobenzene, A new synthetic method of this compound is introduced below., Computed Properties of C6H3BrClF

Example 9: 4- [3- (5-Chloro-2-fluoro-phenyl)-prop-2-ynyl]-piperazine-1- carboxylic acid ethyl ester; 4-Prop-2-ynyl-piperazine-1-carboxylic acid ethyl ester (0.22 g, 0.96 mmol), 2-bromo- 1-chloro-1-fluorobenzene (0.14 mL, 1.2 mmol) and diisopropylamine (0.17 mL, 1.2 mmol) were dissolved in dioxane (1 mL), and the solution degassed with argon for -10 minutes. Bis (methylcyanate) palladium (II) chloride (12 mg, 0.05 mmol), copper iodide (4 mg, 0.02 mmol) and tri-tert-butylphosphine (0.014 mL, 0.06 mmol) were added, and the reaction was sealed and allowed to stir for 16 h. Reaction mixture was diluted with EtOAc (5 mL) and filtered over celite using EtOAc. The organic layer was washed with NH4C1 solution (4 x 10 mL), then dried (Na2S04), filtered and concentrated onto silica gel. Chromatography (SPE) eluting with 30-50 % EtOAc/ hexanes afforded 113 mg (36 %) of the title compound as a yellow oil. 1H NMR (CDC13) 8 (ppm): 7.41 (dd, 1H), 7.26 (ddd, 1H), 7.02 (t, 1H), 4.16 (q, 2H), 3.60 (s, 2 H), 3.56 (t, 4H), 2.61 (t, 4H), 1.28 (t, 3H).

The synthetic route of 1996-30-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB?; NPS PHARMACEUTICALS, INC.; WO2005/80363; (2005); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1996-30-1, name is 3-Bromo-4-fluorochlorobenzene, belongs to chlorides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 1996-30-1, Recommanded Product: 3-Bromo-4-fluorochlorobenzene

To a solution of 2-bromo-4-chloro-l-fluoro-benzene (5 g, 0.0238 mol) in anhydrous diethyl ether (30 mL) was added a 2M solution of n-BuLi in n-hexane (13 mL, 0.0262 mol) at -70 C under nitrogen atmosphere. The reaction mixture was stirred at the same temperature for 30 min. Then, to this reaction mixture was added triisopropyl borate (4.93 g, 0.0262 mol) dropwise. The reaction mixture turned into a white slurry, which was further stirred at -70 C for 30 min and then warmed to RT and stirred for 1 h. The progress of reaction was monitored by TLC and 1H NMR. After completion of the reaction, the mixture was hydro lyzed with 6 N HC1, stirred for lh and the product was extracted with EtOAc (50 mL). The organic layer was washed with brine and concentrated under reduced pressure to obtain a sticky compound which was triturated with n-pentane to afford (5-chloro-2-fluoro-phenyl)boronic acid (2.2 g) as an off white solid

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; MEDIVATION TECHNOLOGIES, INC.; RAI, Roopa; CHAKRAVARTY, Sarvajit; PUJALA, Brahmam; SHINDE, Bharat Uttam; NAYAK, Anjan Kumar; CHAKLAN, Naveen; AGARWAL, Anil Kumar; RAMACHANDRAN, Sreekanth A.; PHAM, Son; WO2015/103355; (2015); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 1996-30-1, A common heterocyclic compound, 1996-30-1, name is 3-Bromo-4-fluorochlorobenzene, molecular formula is C6H3BrClF, 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 solution of 2-bromo-4-chloro-1-fluorobenzene (2.5 mL, 20.52 mmol) and sodiumthiomethoxide (1.453 g, 20.72 mmol) in DMF (20 mL) was stirred at 100 C for 2 h. Thereaction mixture was added to water (20 mL) with stirring, and the aqueous mixture was extracted with ethyl acetate (3 x 50 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo to afford a oily residue that was purified by colunm chromatography on silica gel (hexanes/EtOAc: 20/1) to afford compound I-77a as a colorless oil.?H NMR (600 MHz, DMSO): oe 7.74 (d, J = 8.6, 2.3 Hz, 1 H), 7.49 (dd, J = 8.6, 2.3 Hz, 1 H),7.28 (d, J= 8.6 Hz, 1 H), 2.51 (m, 3 H).

The synthetic route of 1996-30-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; CHILDERS, Matthew L.; DINSMORE, Christopher; FULLER, Peter H.; GUERIN, David J.; KATZ, Jason David; PU, Qinglin; SCOTT, Mark E.; THOMPSON, Christopher F.; ZHANG, Hongjun; CAI, Jiaqiang; DU, Xiaoxing; WANG, Chonggang; KONG, Norman; LIU, Yumei; WO2014/146246; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 1996-30-1, 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. 1996-30-1, name is 3-Bromo-4-fluorochlorobenzene, This compound has unique chemical properties. The synthetic route is as follows.

The title compound (150 mg, 12.7 %, off-white solid) was obtained from [4- [1- (5-] tributylstannanyl-isoxazol-3-yl)-ethyl]-piperazine-l-carboxylic acid ethyl ester (1.063 g, 1.98 mmol) and Pd (PPh3) [2C12] (19.2 mg) with [2-BROMO-4-CHLORO-1-FLUORO-BENZENE] (368mg, 1.76 mmol) in dioxane (lOmL) at 110 [C] overnight. 1H-NMR (CDC13) 8 (ppm): 7.94 (dd, 1H), 7.40 (m, 1H), 7.17 (dd, 1H), 6.71 (d, [1H),] 4.13 (q, 2H), 3.90 (q, 1H), 3.51 (m, 4H), 2.52 (m, 4H), 1.86 (d, 3H) and 1.26 (t, 3H).

The chemical industry reduces the impact on the environment during synthesis 3-Bromo-4-fluorochlorobenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ASTRAZENECA AB; NPS PHARMACEUTICALS, INC.; WO2004/14370; (2004); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1996-30-1, name is 3-Bromo-4-fluorochlorobenzene, belongs to chlorides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 1996-30-1, Application In Synthesis of 3-Bromo-4-fluorochlorobenzene

2-Bromo-6-chloro-3-fluoro-benzaldehyde: To a -78 C. solution of 2-Bromo-4-chloro-1-fluoro-benzene (2.90 g, 13.9 mmol) in 30 mL tetrahydrofuran under an atmosphere of nitrogen was added lithium diisopropylamide solution (1.8M in tetrahydrofuran/heptane/ethylbenzene, 10.0 mL, 18.0 mmol) at such a rate that the internal reaction temperature did not exceed -69 C. After 1 hour at -78 C., dimethylformamide (1.39 mL, 18.0 mmol) was added at such a rate that the internal temperature did not exceed -69 C. After 30 minutes at -78 C., the reaction was quenched with saturated aqueous ammonium hydroxide solution. The resulting mixture was extracted with diethyl ether. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, concentrated in vacuo, and purified by flash chromatography (gradient elution with 0 to 5% ethylacetate/hexanes) to yield 2-Bromo-6-chloro-3-fluoro-benzaldehyde (440 mg, 1.85 mmol). MS (ESI) 236.9 (M+H)+.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Berthel, Steven; Firooznia, Fariborz; Fishlock, Daniel; Hong, Jun-Bae; Lou, Yan; Lucas, Matthew; Owens, Timothy D.; Sarma, Keshab; Sweeney, Zachary Kevin; Taygerly, Joshua Paul Gergely; US2010/222325; (2010); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 1996-30-1, name is 3-Bromo-4-fluorochlorobenzene, molecular formula is C6H3BrClF, 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. Safety of 3-Bromo-4-fluorochlorobenzene

A solution of 2-bromo-4-chloro-1-fluorobenzene (175 .iL, 1.377 mmol) in THF (4.59 mL) at -78 C was treated with n-BuLi (2.6 M, 741 jiL, 1.928 mmol) and the reaction mixture was stirred for 30 mm. To this was added tert-butyl 4- (methoxy(methyl)carbamoyl)piperidine-1-carboxylate (250 mg, 0.918 mmol) in one portion. The cooling bath was removed and the resulting reaction mixture was allowed to warm to rt and stirred for 1.5 h. Purification by automated flash silica gel chromatography using 10% EtOAc in hexanes afforded tert-butyl 4-(5-chloro-2-fluorobenzoyl)piperidine-1-carboxylate (287.9 mg, 92%) as a yellow oil. ESI-MS mlz [M+Na]+ 364.20.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1996-30-1, its application will become more common.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; HITCHCOCK, Stephen; HOPKINS, Maria; KIKUCHI, Shota; MONENSCHEIN, Holger; REICHARD, Holly; SUN, Huikai; MACKLIN, Todd; WO2015/123505; (2015); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1996-30-1, name is 3-Bromo-4-fluorochlorobenzene, belongs to chlorides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 1996-30-1, Application In Synthesis of 3-Bromo-4-fluorochlorobenzene

Step 1: [4-({(l/?,3/?,45)-3-({[ieri-Butyl(dimethyl)silyl]oxy}methyl)-4- [(triisopropylsilyl)oxy]cyclopentyl}amino)pyrimidin-5-yl]{5-chloro-4-[(S)-(5-chloro-2- fluorophenyl)(hydroxy)methyl]-2-thienyl}methanone and Butyl(dimethyl)silyl]oxy}methyl)-4-[(triisopropylsilyl)oxy]cyclopentyl}amino)pyrimidin-5-yl]{5- chloro-4-[(J?)-(5-chloro-2-fluorophenyl)(hydroxy)methyl]-2-thienyl}methanone. [00786] To a solution of 3-bromo- l -chloro-4-fluorobenzene (69.0 uL, 0.57 mmol) in THF (5.00 mL) at 0 C was added dropwise 2 M isopropylmagnesium chloride in Et20 (0.31 mL, 0.62 mmol) and the mixture was stirred at 0 C for 1 hour, and then warmed to rt overnight. This mixture was added dropwise to a solution of lnt-270 ( 185 mg, 0.28 mmol) in THF (8.0 mL) at -40 C and the reaction was allowed to stir at for 30 min at same temperature. The reaction was quenched by addition of saturated NH4C1 and extracted with EtOAc (x2). The combined organic layers were washed with brine, dried over MgS04, and concentrated in vacuo. The residue was purified by ISCO column chromatography (20% EtOAc in hexanes as eluent) to give 0.14g (63%) of the title compounds. LCMS (FA): m/z =782.2 (M+H)

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, 3-Bromo-4-fluorochlorobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; DUFFEY, Matthew O.; ENGLAND, Dylan; FREEZE, Scott; HU, Zhigen; LANGSTON, Steven, P.; MCINTYRE, Charles; MIZUTANI, Hirotake; ONO, Koji; XU, He; (684 pag.)WO2016/4136; (2016); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1996-30-1, name is 3-Bromo-4-fluorochlorobenzene, belongs to chlorides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 1996-30-1, SDS of cas: 1996-30-1

A solution of iso-propylmagnesium chloride in tetrahydrofuran (2M, 106. 6ml) was added dropwise over 15 minutes to a stirred solutionof 2-bromo-4-chloro-1-fluorobenzene (42. 5g) in anhydrous tetrahydrofuran(250ml) at0 C under nitrogen. After a further 15 minutes, a solution ofl-oxa-6-azaspiro [2.5] octane-6-carboxylic acid,1, 1-dimethylethyl ester (43.2g) in anhydrous tetrahydrofuran(50ml) was added followed by copper (I) bromide dimethyl sulphide complex (0.4g). The mixture was stirred at40 C for 18 hours, cooled to20 C, diluted with water(300ml) and extracted with withtert.-butyl methyl ether (2 x300ml). Organic extracts were dried over anhydrous magnesium sulphate, filtered and evaporated under reduced pressure. The residual oil was dissolved in 1,2-dimethoxypropane(200ml). Potassium tert-butoxide (22.8g) was added and the mixture stirred at40 C for 16 hours then at50 C for 24 hours. Further potassium tert.- butoxide (5.7g) was added and stirring continued at50 C for 2 hours then at55 C for 4 hours. Water (500ml) was added and the mixture extracted with tert.-butyl methyl ether (2 x300ml). Organic extracts were dried over anhydrous magnesium sulphate, filtered and evaporated under reduced pressure to give the sub-title compound (47.45g, 67 %) as an oil. ‘H-NMR (400 MHz,CDC13) :8 1.47 (9h, s), 1.67 (2H, td), 1.85-1. 93 (2H, m), 2.94 (2H, s), 3.39 (2H, td), 3.65-3. 80 (2H,m), 6.67(1H, d), 7.06(1H, d), 7.10(1H, s).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Bromo-4-fluorochlorobenzene, and friends who are interested can also refer to it.

Reference:
Patent; ASTRAZENECA AB?; WO2005/49620; (2005); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics