Month: August 2021

Application of 6940-78-9, 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. 6940-78-9, name is 1-Bromo-4-chlorobutane, This compound has unique chemical properties. The synthetic route is as follows.

Step 1: Synthesis of 1-(4-Chlorobutyl)-1,5,6,7-tetrahydroindol-4-one To a solution of 1,5,6,7-tetrahydroindol-4-one (10.0 g, 74.0 mmol) in acetone (300 mL) was added powdered sodium hydroxide (3.26 g, 81.4 mmol) and the mixture stirred at ambient temperature for 0.25 hours. 1-Bromo-4-chlorobutane (9.38 mL, 81.4 mmol) was then added and the resulting mixture stirred at ambient temperature for 7 hours after which time TLC (ethyl acetate:dichloromethane 1:1) showed complete reaction. The reaction was gravity filtered to remove salts, and the filtrate concentrated to dryness under vacuum. The resulting residue was dissolved in dichloromethane (200 mL) and gravity filtered again to remove more salts. The filtrate was then washed with water, dried with sodium sulfate, filtered and the solvent removed under vacuum to yield an oil. Flash chromatography using 6 in. of silica gel in a 5.5 cm column eluding with 1:1 followed by 2:1 ethyl acetate:hexane on half of the residue yielded 9.0 g of an oil which contained ~6.0 g of pure product (72%) and ~3.0 g of acetone aldol condensation product (4-hydroxy-4-methyl-2-pentanone). The oil was taken to the next step without further purification.

The chemical industry reduces the impact on the environment during synthesis 1-Bromo-4-chlorobutane. I believe this compound will play a more active role in future production and life.

Reference:
Patent; HELTON, David; FICK, David; US2009/264443; (2009); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 59681-66-2,Some common heterocyclic compound, 59681-66-2, name is 4-Chloro-N1-methylbenzene-1,2-diamine, molecular formula is C7H9ClN2, 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.

[000316] To a solution of Compound 10B (2.5 g, 16 mmol) in methanol (50 mL) was added triethoxymethane (2.8 g, 19 mmol) and sulfamic acid (155 mg, 1.6 mmol). The mixture was stirred at rt for 5 h. After removal of solvents, the mixture was diluted with water (30 mL) and extracted with ethyl acetate (50 mL x 3). The organic layer was dried over Na2S04. Filtration and evaporation of solvents gave a crude product Compound IOC (2.3 g, crude) as a red solid, which was used to next step without purification. LC-MS (m/z): 167 [M+l]+; 1H-NMR (CDC13, 400 MHz) major characteristic peaks: delta (ppm) 3.84 (s, 3H), 7.30 (d, J= 8.4 Hz, 1H), 7.61 (d, J= 8.8 Hz, 1H), 7.70 (s, 1H), 8.25 (s, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Chloro-N1-methylbenzene-1,2-diamine, its application will become more common.

Reference:
Patent; BIOMARIN PHARMACEUTICAL INC.; WANG, Bing; CHU, Daniel; BRIDGES, Alexander, James; WO2015/42397; (2015); A1;,
Chloride – Wikipedia,
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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. 60811-18-9, name is 4-Bromo-1-chloro-2-fluorobenzene, This compound has unique chemical properties. The synthetic route is as follows., Formula: C6H3BrClF

EXAMPLE 219 (+)-(4aR)-(10bR)-4-methyl-8-(4-chloro-3-fluorophenyl)-10b-methyl-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinolin-3-one STR237 A 15 mL round bottom flask was charged with (+)-(4aR)-(10bR)-4-methyl-10b-methyl-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinolin-3-one-8-boronic acid (178 mg, 0.65 mmol), tetrakis(triphenylphosphine)palladium(0) (23 mg, 0.02 mmol), 1-bromo-4-chloro-3-fluorobenzene (136 mg, 0.65 mmol), 0.65 mL of 2M sodium carbonate and 2 mL of THF, fitted with a reflux condenser, and the stirred mixture was heated at 80, under nitrogen, for 24 h. The mixture was cooled, diluted with ethyl acetate (75 mL) and washed with brine (2*25 mL). The combined organic extracts were dried over sodium sulfate, concentrated, and purified by silica gel chromatography (ethyl acetate eluent) to give 125 mg (56%) of the title compound as an amorphous foam. FDMS: m/e=357. alpha[D]589 =+74.28 (c=0.35, chloroform).

According to the analysis of related databases, 60811-18-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Eli Lilly and Company; US5578724; (1996); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 39226-96-5, A common heterocyclic compound, 39226-96-5, name is (2-Chloro-3-(trifluoromethyl)phenyl)methanamine, molecular formula is C8H7ClF3N, 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.

Example 59 N-{[2-Chloro-3-(trifluoromethyl)phenyl]methyl}-3-methyl-1-(1-methyl- 1 H-imidazol-2-yl)-2-oxo-4-imidazolidinecarboxamide (E59) (in a form obtainable or prepared from (4S)-2-oxo-3-{[(phenylmethyl)oxy]carbonyl}-4-imidazolidinecarboxylic acid); A solution of 3-methyl-1-(1-methyl-1 H-imidazol-2-yl)-2-oxo-4-imidazolidinecarboxylic acid (166 mg, 0.517 mmol) and N-ethyl morpholine (0.397 ml, 3.10 mmol) in dichloromethane (5 ml) was treated with 1-hydroxybenzotriazole hydrate (95 mg, 0.620 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (99 mg, 0.517 mmol) and stirred at room temperature for 10 minutes. 1-[2-Chloro-3- (trifluoromethyl)phenyl]methanamine (108 mg, 0.517 mmol) was then added and the reaction stirred overnight at room temperature. The reaction mixture was diluted with dichloromethane and washed with saturated sodium hydrogen carbonate solution, water and brine, separated through a hydrophobic frit and the organic layer was reduced under vacuum. The residue was purified by mass-directed automated HPLC to give N-{[2-chloro-3-(trifluoromethyl)phenyl]methyl}-3-methyl-1-(1-methyl-1 H- imidazol-2-yl)-2-oxo-4-imidazolidinecarboxamide (67 mg, 29.6 % yield). LC/MS [M+H]+ = 416, retention time = 1.89 minutes.

The synthetic route of 39226-96-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2008/119825; (2008); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 39065-95-7,Some common heterocyclic compound, 39065-95-7, name is 4-(Chlorodifluoromethoxy)aniline, molecular formula is C7H6ClF2NO, 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.

To a solution of 1-methyl-7-(pyrimidin-5-yl)-1H-benzo[d]imidazole-5-carboxylic acid (1g, 0.04 g, 0.157 mmol, 1 eq) and 4-(chlorodifluoromethoxy)aniline (33.50 mg, 0.173 mmol, 1.1 eq), HATU (71.79 mg, 0.189 mmol, 1.2 eq) in DMF (1 mL) at 15 C. was added DIEA (61.00 mg, 0.472 mmol, 82.21 uL, 3 eq). The mixture was stirred at 15 C. for 12 hours. LCMS showed ig was consumed completely and desired mass was detected. The mixture was concentrated, and the resulting residue was purified by prep-HPLC (FA condition, column: Luna C18 100*30 5u; mobile phase: [water (0.225% FA)-ACN]; B %: 35%-50%, 14 min) to afford the title compound 1 as a yellow solid. 1H NMR (400 MHz, MeOD-d4) delta 1N NMR (400 MHz, MeOD-d4) delta 9.31 (s, 1H), 9.06 (s, 2H), 8.45 (d, J=1.5 Hz, 1H), 8.39 (s, 1H), 7.91 (d, J=1.5 Hz, 1H), 7.84 (d, J=9.0 Hz, 2H), 7.31 (d, J=9.0 Hz, 2H), 3.60 (s, 3H).

The synthetic route of 39065-95-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Terns, Inc.; ROMERO, F. Anthony; KIRSCHBERG, Thorsten A.; HALCOMB, Randall; XU, Yingzi; (144 pag.)US2020/87283; (2020); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 19752-55-7,Some common heterocyclic compound, 19752-55-7, name is 1-Bromo-3,5-dichlorobenzene, molecular formula is C6H3BrCl2, 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.

To 5.1 g (0.209 mol) of magnesium turnings were added 0.45 g of a 1 molar solution of DIBAL in hexane at 60°C. After 15 min, 3,5-dichloro-bromobenzene (5.0 g, 0.022 mol) and 25 mL THF were added and the mixture was stirred. After start up of the reaction a mixture of 45g (0.2 mol) 3,5-dichloro-bromobenzene and 250 mL THF was added under reflux. After completion of the reaction the mixture was cooled to 0°C and 31 .1 g (0.219 mol) of ethyl trifluoroacetate were added. After 2 h an aqueous solution of NH4CI was added and the mixture was separated between MTBE and aqueous N H4CI solution. The organic layer was separated and the solvent was removed in vacuum. (34.3g brown oil; purity 70percent acc. to g.c; yield 50percent)1H-NMR (360 MHz, CDCI3): delta = 7.7 (s, 1 H), 7.9 (s, 2H) ppm.

The synthetic route of 19752-55-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BASF SE; KOeRBER, Karsten; KORDES, Markus; RACK, Michael; VON DEYN, Wolfgang; KAISER, Florian; WO2012/59441; (2012); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 39065-95-7,Some common heterocyclic compound, 39065-95-7, name is 4-(Chlorodifluoromethoxy)aniline, molecular formula is C7H6ClF2NO, 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 suspension of 3-bromo-4-fluoro-5-nitrobenzoic acid (24b, 150 mg, 0.568 mmol) in SOCl2 (2 mL) was stirred at 60 C. for 3 hours. The mixture was concentrated to obtain 3-bromo-4-fluoro-5-nitro-benzoyl chloride (214 mg, crude) as a white solid. To a mixture of 4-(chlorodifluoromethoxy)aniline (1h, 146.64 mg, 0.758 mmol) and pyridine (89.89 mg, 1.13 mmol, 91.72 uL) in THF (2 mL) under N2 was added 3-bromo-4-fluoro-5-nitro-benzoyl chloride (213.97 mg, 0.758 mmol). The mixture was stirred at 20 C. for 3 hours. LCMS showed the desired MS. The mixture was extracted with ethyl acetate (2 mL*3), the combined organic layers were washed with brine (5 mL*2), dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by prep-TLC (SiO2, petroleum ether:ethyl acetate=1: 1, Rf=0.3). Compound 24c was obtained as a white solid.

The synthetic route of 39065-95-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Terns, Inc.; ROMERO, F. Anthony; KIRSCHBERG, Thorsten A.; HALCOMB, Randall; XU, Yingzi; (144 pag.)US2020/87283; (2020); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 2106-02-7,Some common heterocyclic compound, 2106-02-7, name is 2-Chloro-4-fluoroaniline, molecular formula is C6H5ClFN, 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.

Into a 20-L 4-neck round flask was placed a solution of2-chloro-4-fluorobenzenamine (1300 g, 8.82 mol, 1.00 equiv, 99%) in toluene (10 L), 4-methylbenzenesulfonic acid (3.1 g, 17.84 mmol, 99%), and hexane-2,5-dione (1222.5 g, 10.62 mol, 1.20 equiv, 99%). The resulting solution was heated to reflux for 1 h in an oil bath and cooled. The pH value of the solution was adjusted to 8 with sodium carbonate (1 mol/L). The resulting mixture was washed with 1×5000 mL of water and concentrated under vacuum. The crude product was purified by distillation and the fraction was collected at 140 0C to afford l-(2-chloro-4-fluorophenyl)-2,5-dimethyl-lH-pyrrole (1700 g, yield: 85%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Chloro-4-fluoroaniline, its application will become more common.

Reference:
Patent; ARRAY BIOPHARMA INC.; GENENTECH, INC.; ALIAGAS, Ignacio; GRADL, Stefan; GUNZNER, Janet; MATHIEU, Simon; PULK, Rebecca; RUDOLPH, Joachim; WEN, Zhaoyang; GRINA, Jonas; HANSEN, Joshua D.; LAIRD, Ellen; MORENO, David; REN, Li; WENGLOWSKY, Steven Mark; WO2011/25940; (2011); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 694-80-4, These common heterocyclic compound, 694-80-4, name is 1-Bromo-2-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.

Add to Schlenk tubeN- (2-mercapto) acetamide(0.3 mmol, 50.1 mg), FeSO47H2O (0.06 mmol, 16.68 mg),1,10-lindolinol (0.06 mmol, 10.8 mg) andPotassium tert-butoxide (1.2 mmol, 134.4 mg)With nitrogen to protect the reaction system (pumping gas three times),1,2-dibromobenzene (0.45 mmol, 105.2 mg) and DMF (2 mL) were added to the reaction system with a syringe,Heated to 135 C,Stirring reaction 24hAfter completion of the reaction, the mixture was cooled to room temperature,20 mL of water was added and extracted three times with ether,The organic phase was washed with water, dried over anhydrous sodium sulfate,Column chromatography to obtain the product10H-phenothiazine. Yield 70%.Using a method similar to that of Example 1,Respectively, with o-bromobenzene,O-bromochlorobenzene,O-chlorobenzene,O-dichlorobenzene was used in place of o-dibromobenzene in Example 1 to give the product phenothiazine in a yield of 72%, 81%80%, 20%.

Statistics shows that 1-Bromo-2-chlorobenzene is playing an increasingly important role. we look forward to future research findings about 694-80-4.

Reference:
Patent; Suzhou University; Zhang, Songlin; Hu, Weiye; Zheng, Songlin; Wu, San; Wang, Ru; Zhang, Fang; (7 pag.)CN104311508; (2017); B;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 1996-29-8, These common heterocyclic compound, 1996-29-8, name is 1-Bromo-4-chloro-2-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.

A solution of compound 40-a-1 (1 g, 4.77 mmol) in anhydrous tetrahydrofuran was added dropwise to a solutionof LDA (2M, 3 ml) in tetrahydrofuran at -50 C. After the addition was completed, the mixture was stirred for 30 minutesat -50 C. To the above reaction mixture was added methyl iodide (1037 mg, 7.30 mmol) at -50 C. The reaction mixturewas then allowed to naturally warm to room temperature, poured into water and extracted with ethyl acetate. The organicphase was washed with saturated brine, dried and concentrated, and the crude product was purified by column chromatography(100% petroleum ether) to give compound 40-a (747 mg) as a colorless oil, purity 77%, yield 70%, MSm/z(ESI):N/A

Statistics shows that 1-Bromo-4-chloro-2-fluorobenzene is playing an increasingly important role. we look forward to future research findings about 1996-29-8.

Reference:
Patent; Shanghai Haiyan Pharmaceutical Technology Co., Ltd.; Yangtze River Pharmaceutical Group Co., Ltd.; LAN, Jiong; ZHOU, Fusheng; ZHAO, Jinzhu; HUANG, Dong; XIE, Jing; HU, Yi; LV, Qiang; (63 pag.)EP3412653; (2018); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics