Category: 33863-76-2

Adding a certain compound to certain chemical reactions, such as: 33863-76-2, name is 1-Bromo-3-chloro-5-fluorobenzene, 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 33863-76-2, Safety of 1-Bromo-3-chloro-5-fluorobenzene

Preparation 32 1-Bromo-3-chloro-5-methoxybenzene Sodium methoxide (2.20 ml of a 4.5M solution in methanol, 10.0 mmol) was added dropwise to a stirred solution of 1-fluoro-3-chloro-5-bromobenzene (1.00 g, 4.77 mmol) in methanol (28 ml) at room temperature under nitrogen. The reaction was heated under reflux for 3 days and cooled to room temperature. The mixture was concentrated under reduced pressure and the resulting yellow oil was dissolved in dichloromethane (30 ml). The resulting solution was washed with water (2*20 ml) dried over magnesium sulphate, filtered and concentrated under reduced pressure. The crude product was purified by flash column chromatography on silica gel eluding with cyclohexane to provide the title compound (302 mg) as a colourless oil. 1H-NMR (400 MHz, CDCl3): delta=3.77 (s, 3H), 6.82 (s, 1H), 6.94 (s, 1H), 7.09 (s, 1H). Microanalysis: Found: C, 37.94; H, 2.75. C7H6BrClO requires C, 37.96; H, 2.73%.

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-chloro-5-fluorobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Jones, Lyn Howard; Mowbray, Charles Eric; Price, David Anthony; Selby, Matthew Duncan; Stupple, Paul Anthony; US2003/100554; (2003); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 33863-76-2, 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. 33863-76-2 name is 1-Bromo-3-chloro-5-fluorobenzene, 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.

Sodium methoxide (4.5M solution in methanol, 2.20 [ML,] 10.0 [MMOL)] was added dropwise to a stirred solution of 1-fluoro-3-chloro-5-bromobenzene (1.00 g, 4.77 [MMOL)] in methanol (28 [ML)] at room temperature under a nitrogen atmosphere. The mixture was heated at reflux for 3 days and then cooled to room temperature. The mixture was evaporated under reduced pressure and the resulting yellow oil was dissolved in [DICHLOROMETHANE] (30 [ML).] The [DICHLOROMETHANE] solution was washed with water [(2X20] [ML)] dried over magnesium sulphate, filtered and evaporated under reduced pressure. The residue was purified by chromatography on silica gel eluting with cyclohexane to provide the title compound as a colourless oil (302 mg). [1 H-NMR (400MHZ, CDC13)] : [8] 3.77 (s, 3H), 6.82 (s, 1 H), 6.94 (s, 1 H), 7.09 (s, [1 H).] Microanalysis : Found: C, 37.94 ; H, 2.75. [C7H6BRCIO] requires ; C, 37.96 ; H, 2.73%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-3-chloro-5-fluorobenzene, and friends who are interested can also refer to it.

Reference:
Patent; PFIZER LIMITED; PFIZER INC.; WO2004/29051; (2004); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 33863-76-2, 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. 33863-76-2, name is 1-Bromo-3-chloro-5-fluorobenzene, This compound has unique chemical properties. The synthetic route is as follows.

Preparation 6TERT-BUTYL 3-(3-CHLORO-S-FLUOROPHENYL)-S-HYDROXYAZETIDINE-I – CARBOXYLATE5 A mixture of 1 -bromo-3-chloro-5-fluorobenzene (1.47 g, 7.01 mmol),, magnesium turnings (0.82 g, 31.1 mmol) and a small piece of iodine in dry tetrahydrofuran (50 mL), under nitrogen was gently heated until reaction started and stirred for 1 h at ambient temperature after which a solution of 1 -Boc-3-azetidinone (1.0 g, 5.85 mmol) in dry diethyl ether (10 mL) was added dropwise. The resulting10 mixture was stirred for 15 min and water (70 ml) and saturated aqueous ammonium chloride (20 mL,) was added and the mixture was extracted with ethyl acetate (2×50 ml). The combined organic phase was dried (Na2SO4), filtered and evaporated to dryness. The crude product was purified by flash column chromatography on silica gel (ethylacetate/isooctane 1 :4 to 1 : 1 ) to give the title compound Yield: 1.25 g. MS m/z15 (rel. intensity, 70 eV) 285 (M+, 1 ), 156 (60), 141 (43), 127 (80), 57 (bp).

The chemical industry reduces the impact on the environment during synthesis 1-Bromo-3-chloro-5-fluorobenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; NSAB, FILIAL AF NEUROSEARCH SWEDEN AB, SVERIGE; SONESSON, Clas; SWANSON, Lars; PETTERSSON, Fredrik; WO2010/58020; (2010); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

33863-76-2, name is 1-Bromo-3-chloro-5-fluorobenzene, belongs to chlorides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. category: chlorides-buliding-blocks

In a three-necked flask equipped with a magnetic stirrer and placed under a nitrogen atmosphere, tert-butyl (R)-2-formylpiperidine-1-carboxylate (3.7 g, 17.3 mmol) is dissolved in tetrahydrofuran (50 mL). (3-Chloro-5-fluorophenyl) bromide (0.5 M solution in THF) (41.6 mL, 20.8 mmol) is added dropwise at -70 C. The mixture is stirred at -70 C. for 5 hours and then hydrolyzed by addition of water at 0 C. The medium is diluted with EtOAc, washed with water and with saturated NaCl solution and then dried over MgSO4 and concentrated by evaporation under reduced pressure (RP). The residue is purified by chromatography on silica gel eluted with a 6/2 cyclohexane/EtOAc mixture. 1.28 g of tert-butyl (2R)-2-[(S)-(3-chloro-5-fluorophenyl)(hydroxy)methyl]piperidine-1-carboxylate are thus obtained in the form of an oil that crystallizes, and 1.27 g of tert-butyl (2R)-2-[(R)-(3-chloro-5-fluorophenyl)(hydroxy)methyl]piperidine-1-carboxylate are obtained in the form of an oil that crystallizes. tert-Butyl (2R)-2-[(S)-(3-chloro-5-fluorophenyl)(hydroxy)methyl]piperidine-1-carboxylate: (M+Na)+=366; [alpha]D20 C.=+16.4+-0.6 (MeOH) and tert-butyl (2R)-2-[(R)-(3-chloro-5-fluorophenyl)(hydroxy)methyl]piperidine-1-carboxylate: (M+Na)+=366; [alpha]D20 C.=-46.1+-0.9 (MeOH)

The synthetic route of 33863-76-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SANOFI-AVENTIS; US2010/298377; (2010); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 33863-76-2, 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. 33863-76-2, name is 1-Bromo-3-chloro-5-fluorobenzene, This compound has unique chemical properties. The synthetic route is as follows.

To a degassed solution of (R)-3-((R)-3-Amino-2-oxo-perhydro- azepin-l-yl)-piperidine-l -carboxylic acid tert-butyl ester 39.6 (0.6 g, 1.9 mmol) in toluene (40 mL) was added sodium tert-butoxide (0.34 g, 3.6 mmol), (R)-(+)-2,2′-bis(diphenylphosphino)- Iota , -binaphthyl (0.20 g, 0.33 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.1 1 g, 0.12 mmol) and l-Bromo-3-chloro-5-fluoro-benzene (0.5 g, 2.4 mmol). The solution was purged under an atmosphere of argon and heated to reflux for 2.5 h. The reaction was cooled to room temperature, filtered through celite pad, diluted with ether and washed with a solution of NaHC03, brine, dried(Na2SC>4) filtered and solvent was concentrated in vacuo to afford a residue which purified by flash chromatography (gradient DCM/MeOH, 0 to 5%) to afford 0.4g, 48.2%. LCMS m z 385.4 [M – tBu]+.

The chemical industry reduces the impact on the environment during synthesis 1-Bromo-3-chloro-5-fluorobenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BIOGEN IDEC MA INC.; ERLANSON, Daniel, A.; MARCOTTE, Doug; KUMARAVEL, Gnanasambandam; FAN, Junfa; WANG, Deping; CUERVO, Julio, H.; SILVIAN, Laura; POWELL, Noel; BUI, Minna; HOPKINS, Brian, T.; TAVERAS, Art; GUAN, Bing; CONLON, Patrick; ZHONG, Min; JENKINS, Tracy, J.; SCOTT, Daniel; SUNESIS PHARMACEUTICALS, INC.; LUGOVSKOY, Alexey, A.; WO2011/29046; (2011); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 33863-76-2,Some common heterocyclic compound, 33863-76-2, name is 1-Bromo-3-chloro-5-fluorobenzene, 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.

Step 1 : 1-Bromo-3-chloro-5-methoxybenzene. 1 -Bromo-3-chloro-5-fluorobenzene (1 g, 4.77 mmol, 1 equiv.) was treated at 0 C with sodium methoxide (25 % in MeOH, 1.2 ml_, 5.71 mmol, 1.2 equiv.). The reaction mixture was stirred at 100 C for 3 h. The solution was concentrated under reduced pressure, the crude product was extracted with DCM, washed with H20, brine, dried over MgS04 and concentrated. The product was obtained as a white solid (747 mg, 71 %). LCMS [M+H]+ 220; 1 H NMR (400 MHz, CD3CI) 5 7.09 (1 H, t, J = 1 .7 Hz), 6.94 – 6.92 (1 H, m), 6.83 – 6.80 (1 H, m), 3.77 (3H, s).

The synthetic route of 33863-76-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THOMAS HELLEDAYS STIFTELSE FOeR MEDICINSK FORSKNING; SCOBIE, Martin; WALLNER, Olov; KOOLMEISTER, Tobias; VALLIN, Karl Sven Axel; HENRIKSSON, Carl Martin; HOMAN, Evert; HELLEDAY, Thomas; JACQUES, Sylvain; DESROSES, Matthieu; JACQUES-CORDONNIER, Marie-Caroline; FISKESUND, Roland Julius Yu; (359 pag.)WO2015/187089; (2015); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

A common heterocyclic compound, 33863-76-2, name is 1-Bromo-3-chloro-5-fluorobenzene, 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. 33863-76-2.

EXAMPLE 8.0 8-(1-(3-chloro-5-fluorophenylamino)ethyl)-N,N-dimethyl-2-morpholino-4-oxo-4H-chromene-6-carboxamide (single enantiomer) To a mixture of 8-(1-aminoethyl)-N,N-dimethyl-2-morpholino-4-oxo-4H-chromene-6-carboxamide (350 mg, 1.01 mmol, single enantiomer, [alpha]D20: +35 in acetonitrile), cesium carbonate (1288 mg, 3.95 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (147 mg, 0.25 mmol) and 1-bromo-3-chloro-5-fluorobenzene (467 mg, 2.23 mmol) in degassed 1,4-dioxane (2 ml), was added tris(dibenzylideneacetone)dipalladium (70 mg, 0.08 mmol). The suspension was heated in a sealed container at 95 C. for 16 hrs. The reaction mixture was filtered through a short pad of dicalite and concentrated under reduced pressure. The crude product was purified by flash chromatography on silica gel eluting with 0 to 8% isopropanol in DCM. The solvent was evaporated to dryness, the product triturated with diethyl ether-DCM (9:1), collected by filtration and dried to afford 8-(1-(3-chloro-5-fluorophenylamino)ethyl)-N,N-dimethyl-2-morpholino-4-oxo-4H-chromene-6-carboxamide (320 mg; 67%) as a clear yellow solid. Mass Spectrum: M+H+ 474. [alpha]D20: -138. NMR Spectrum (DMSOd6): 1.52 (d, 3H), 2.75 (bs, 3H), 2.95 (bs, 3H), 3.49-3.63 (m, 4H), 3.70-3.79 (m, 4H), 4.98-5.07 (m, 1H), 5.60 (s, 1H), 6.23 (d, 1H), 6.42 (d, 1H), 6.43 (ddd, 1H), 6.94 (d, 1H), 7.54 (d, 1H), 7.80 (d, 1H).

The synthetic route of 1-Bromo-3-chloro-5-fluorobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; US2011/98271; (2011); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

These common heterocyclic compound, 33863-76-2, name is 1-Bromo-3-chloro-5-fluorobenzene, 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. 33863-76-2

EXAMPLE 13-Chloro-5-{[5-chloro-l-(lH-pyrazolo[3,4-]pyridin-3-ylmethyl)-lH-indazol-4- yl] oxy } benzonitrileStep 1 : 3-Bromo-5-chlorophenyl 2-chloro-5-fluorophenyl ether; To a solution of 2-chloro-5-fluorophenol ( 82.3 g, 562 mmol) and l-bromo-3- chloro-5-fluorobenzene (124g, 590 mmol) in NMP (200 mL) was added potassium carbonate (155g, 1.123mol). The resulting mixture was then heated to 1400C and maintained at 14O0C for 30 hours, after which the mixture was poured into water (1500 mL) and extracted with EtOAc (2500 + 1500 mL). The combined extracts were washed with water and brine. This solution was concentrated on the rotary evaporator and the residue was distilled at high vacuum at 135-1900C to give the title compound as a clear, colorless liquid. leta NMR (CDCI3) delta 7.45 (dd, 1eta, J=9.0 and 4.5 hz), 7.28(dd, 1eta, J=I .7Hz), 7.26(s, IH), 7.00(dd, Ih, J=I .95Hz), 6.92(ddd, IH, J=10.5, 7.6 and 2.7Hz), 6.89(dd, IH, J=I.95Hz).

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 33863-76-2.

Reference:
Patent; MERCK & CO., INC.; WO2008/76223; (2008); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

33863-76-2, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 33863-76-2 as follows.

A solution of 1-bromo-3-chloro-5-fluorobenzene (50.0 g, 239 mmol) in DMF (300 ml.) was treated with sodium methoxide (15.5 g, 286 mmol) and the reaction was stirred overnight at rt. The mixture was diluted with ethyl acetate (500 mL) and washed with water (700 mL). The organic layer was isolated, washed with brine, dried over magnesium sulfate, filtered, and concentrated to give 51.0 g of the title compound which was used without purification. 1H NMR (DMSO-c/6) delta 7.23 (t, 1 H), 7.13 – 7.15 (m, 1 H), 7.05 (t, 1 H), 3.77 (s, 3 H).

According to the analysis of related databases, 1-Bromo-3-chloro-5-fluorobenzene, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2008/157273; (2008); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 33863-76-2 name is 1-Bromo-3-chloro-5-fluorobenzene, 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. 33863-76-2

To a solution of 1-bromo-3-chloro-5-fluorobenzene (25 g, 120 mmol) in methanol (800 ml) was added sodium methoxide (64 g, 1180 mmol). The reaction was heated to reflux for 9 days. The reaction was then concentrated in vacuo to one fifth of the volume (150 ml), cooled, and water (1000 ml) added. The mixture was extracted with diethyl ether (3 x 150 ml). The combined organic extracts were washed with brine (2 x 100 ml), dried over Na2SO4 and evaporated to afford the title compound (24.6 g). 1HNMR (CDCI3): 3.80(s, 3H), 6.84(s, 1 H), 6.96(s, 1 H), 7.10 (s, 1 H)GCMS Rt=3.86min MS m/z 222 [MH]+

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-3-chloro-5-fluorobenzene, and friends who are interested can also refer to it.

Reference:
Patent; PFIZER LIMITED; WO2008/135826; (2008); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics