Month: March 2021

Reference of 57946-63-1,Some common heterocyclic compound, 57946-63-1, name is 2-Bromo-4-(trifluoromethyl)aniline, molecular formula is C7H5BrF3N, 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 round-bottom flask was charged with 2-bromo-4-(trifluoromethyl)aniline (4.115 g, 17.14 mmol), l-methyl-5-(4,4,5,5-tetramethyl-l ,3,2-dioxaborolan-2-yl)-lH- pyrazole (4.64 g, 22.29 mmol), potassium phosphate (10.92 g, 51.4 mmol), and Pd(AmPhos)2Ci2 (0.607 g, 0.857 mmol). Dioxane (30 mL) and water (10 mL) were added to give a thick suspension. The flask was fitted with a reflux condenser and placed in a 90 ¡ãC oil bath for 4 h. The mixture was removed from the heat, then diluted with water and extracted with EtOAc (3x). The combined organic extracts were dried over sodium sulfate, filtered and concentrated. The residue was partially purified twice by chromatography on silica gel, first with 25 to 75percent EtO Ac/Heptane, then with 20 to70percent EtO Ac/Heptane. The partially purified material thus obtained was dissolved in methanol and loaded onto a lOg SCX-2 ion exchange column. The column was eluted with methanol, then with 2N ammonia in methanol. The basic fractions were combined and concentrated to give 2-(l-methyl-lH-pyrazol-5-yl)-4-(trifluoromethyl)aniline (0.5526 g, 2.291 mmol, 13.36 percent yield) as a tan solid. 1H NMR (400 MHz, DMSO-d6) delta = 7.52 (d, J = 1.9 Hz, 1 H), 7.43 (ddd, J = 0.5, 2.3, 8.6 Hz, 1 H), 7.26 (d, J = 1.9 Hz, 1 H), 6.88 (d, J = 8.5 Hz, 1 H), 6.32 (d, J = 1.9 Hz, 1 H), 5.62 (s, 2 H), 3.64 (s, 3 H). m/z (ESI) 242.2 (M+H)+.

The synthetic route of 57946-63-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DINEEN, Thomas; MARX, Isaac, E.; NGUYEN, Hanh, Nho; WEISS, Matthew; AMGEN INC.; WO2013/25883; (2013); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 112734-22-2,Some common heterocyclic compound, 112734-22-2, name is (4-Bromo-2-fluorophenyl)methanamine, molecular formula is C7H7BrFN, 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 : N-(4-Bromo-2-fluorobenzyl)-l-phenylmethanesulfonamide To a solution of (4-bromo-2-fluoro-phenyl)methanamine (3 g, 14.7 mmol) in dichloromethane (50 mL) was added N,N-diisopropylethylamine (3.3 mL, 19.1 mmol), followed by phenylmethanesulfonyl chloride (3.3 g, 17.6 mmol) and the reaction was stirred at ambient temperature for 3 hours. The reaction was diluted with dichloromethane and washed with water and brine, dried with MgS04, concentrated and purified by silica gel column chromatography (20-100% EtOAc in heptane) to give N- [(4-bromo-2-fluoro-phenyl)methyl]-l-phenyl-methanesulfonamide (4.22 g, 80% yield). LCMS (m/z) ES+ 358 [M+l]+.

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

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; FAUBER, Benjamin; RENE, Olivier; WO2013/92941; (2013); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 5433-01-2, 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 5433-01-2 as follows.

To a solution of 1 -bromo-3-isopropylbenzene (10 g, 0.05 moi) in THF was added dropwise with BuLi (47 ml,, 0.075 niol) at -60 ‘C. After stirred 30 minutes, N-methoxy-N-methyiacetamide (6.22 g, 0.06 mol) was added. The mixture was stirred at -30C for 3 hours. Then the mixture was quenched with H20, the mixture was partitioned between EtOAc and water. The layer was separated and washed with water, brine, dried over Na2SC>4, and concentrated. The residue was purified by column chromatography to obtained the titled compound. ? NMR (CHLQRQFORM-d): delta 7.85 (s, i l l ). 7.79 (dt, j = 7.6, 1 .4 Hz, 1H), 7.33 – 7.53 (m, 2H), 3.00 (dt, J – 13.8, 6.9 Hz, 1H), 1.30 (d, J – 6.7 Hz, 6H)

According to the analysis of related databases, 5433-01-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; RIPKA, Amy, S.; SAUNDERS, Jeffrey, O.; KAMENECKA, Theodore, Mark; GRIFFIN, Patrick, R.; WO2013/78233; (2013); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 4885-18-1, name is 1-(3-Bromophenyl)-N,N-dimethylmethanamine, molecular formula is C9H12BrN, 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 1-(3-Bromophenyl)-N,N-dimethylmethanamine

(ii) 3-Bromo-N,N-dimethylbenzylamine (21.4 g) was reacted with magnesium turnings (2.4 g) in dry tetrahydrofuran (75 ml). The mixture was cooled to 0 and gaseous formaldehyde (generated by heating 15 g paraformaldehyde in a stream of argon) was passed over the stirred solution. Tetrahydrofuran (25 ml) was added and the mixture was stirred at room temperature for 2.5 hours and acidified to pH 1. The mixture was extracted with aqueous 3N hydrochloric acid, and the aqueous extracts were made alkaline with aqueous sodium hydroxide and extracted with ether. The ether extracts were evaporated to give 3-(dimethylaminomethyl)benzyl alcohol (14.78 g, 78%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4885-18-1, its application will become more common.

Reference:
Patent; Smith Kline & French Laboratories Limited; US4496567; (1985); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 7051-34-5,Some common heterocyclic compound, 7051-34-5, name is (Bromomethyl)cyclopropane, molecular formula is C4H7Br, 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.

Intermediate Preparation 7; 2-Cvclopropylmethyl-ri,3″|dithiane-2-carboxylic acid ethyl ester; To a flamed dried flask is added dry toluene (80 mL) and sodium hydride (60%, 33.5 mmol, 1.34 g). The reaction is cooled in a ice bath and a solution of ethyl 1,3 dithiane carboxylate (52 mmol, 10 g) and bromomethyl cyclopropane (62.4 mmol, 8.42 g) in DMF (24 mL) are added dropwise over 10 minutes. The ice bath is removed and the reaction is stirred for 18 h. Water is added (50 mL) and the organic layer is separated. The organic layer is washed with brine, dried (Na2SO4), and concentrated to a yellow oil (12 g, 92 %). LC-ES/MS: 247.0 (M+ 1).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (Bromomethyl)cyclopropane, its application will become more common.

Reference:
Patent; ELI LILLY AND COMPANY; WO2009/12125; (2009); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 38573-88-5, name is 1-Bromo-2,3-difluorobenzene, A new synthetic method of this compound is introduced below., Application In Synthesis of 1-Bromo-2,3-difluorobenzene

Preparation 81 ,3-DICHLORO-2-(2,3-DIFLUOROPHENYL)PROPAN-2-OLTo a solution of 1-bromo-2,3-difluorobenzene (19.5 g, 0.10 mol) in dry diethyl30 ether (120 mL) at -780C, under nitrogen was added n-hexyl lithium (2.3 M in hexane, 41.7 ml, 0.096 mol) dropwise. The mixture was stirred for 1 min after which a solution of 1 ,3-dichloroacetone (12.2 g, 0.096 mol) in dry diethyl ether (30 mL) was added dropwise. The resulting mixture was stirred at -780C for 1 h and then brought to ambient temperature and stirred for 1 h. Aqueous hydrochloric acid (50 mL. 10percent) was35 added and the mixture was extracted with ethylacetate (2×50 ml). The combined organic phase was washed with brine, dried (Na2SO4), filtered and evaporated to dryness. The crude product was purified by flash column chromatography on silica gel (ethylacetate/isooctane, 1 :9 to 1 :1 ) to give the title compound (1 1 .8 g, 48percent). MS m/z (rel. intensity, 7O eV) 241 (M+, 1 ), 193 (33), 191 (bp), 141 (1 1 ), 127 (68).

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; NSAB, FILIAL AF NEUROSEARCH SWEDEN AB, SVERIGE; SONESSON, Clas; SWANSON, Lars; PETTERSSON, Fredrik; WO2010/58020; (2010); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 103977-79-3, The chemical industry reduces the impact on the environment during synthesis 103977-79-3, name is 3-Bromo-2,4-difluoroaniline, I believe this compound will play a more active role in future production and life.

C. Ethyl 7-bromo-6,8-difluoro-4-hydroxyquinoline-3-carboxylate A stirred mixture of 26 g of 3-amino-2,6-difluorobromobenzene and 27 g of diethyl ethoxymethylenemalonate was heated at 150 C. for 1 hour. After cooling, 100 ml of Dowtherm “A” (commercially available high boiling inert solvent mixture of diphenylether and dibenzofuran) was added and the mixture was heated under nitrogen at 260 C. for 1.5 hour. The mixture was cooled to room temperature and 200 ml of hexanes was added. The resulting precipitate was collected by filtration, washed with hexanes and dried to give a cream solid, m.p. 285 C., yield 78% (32.32 g).

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-2,4-difluoroaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Pfizer Inc.; US4623650; (1986); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 39478-78-9, The chemical industry reduces the impact on the environment during synthesis 39478-78-9, name is 5-Bromo-2-methylaniline, I believe this compound will play a more active role in future production and life.

General procedure: An oven-dried Schlenk tube with the presence of magnetic stir bar which is Teflon-coated was charged with Pd(dba)2 (11.5 mg, 0.02 mmol, 2 mol%) and ligand L4 (8.4 mg, 0.02 mmol, 2 mol%). The flask was evacuated and backfilled with nitrogen (3 cycles). Pre-complexation of palladium and ligand was initiated by injecting freshly distilled dry dichloromethane (2.0 mL) and Et3N (0.1 mL) into the tube. The solution was stirred and warmed with hair drier till the solvent condensed on the tube wall. The solvent was removed under vacuum. Aryl bromide (1.0 mmol), KOt-Bu (0.25 mmol), and potassium hexacyanoferrate(II) trihydrate (0.23 mmol) were charged successively to the tube followed by another 3 evacuation-nitrogen refill cycles. Water (1.0 mL) and acetonitrile (1.0 mL) were used as a solvent mixture. The tube was immersed into a preheated 50 C oil bath for 24 hours. The reaction was quenched by cooling to ambient temperature and added with EtOAc and water. The organic supernatant was analyzed by GC. The organic layer was separated and the remained aqua medium was further extracted with EtOAc (10 mL ¡Á 3). The combined organic phases were concentrated under reduced pressure. The crude product was purified by flash column chromatography on silica gel (230-400 mesh). The pure fractions were collected, dried under vacuum, and followed by proton (1H) and carbon (13C) NMR characterization

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, 5-Bromo-2-methylaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Yeung, Pui Yee; Tsang, Chun Pui; Kwong, Fuk Yee; Tetrahedron Letters; vol. 52; 52; (2011); p. 7038 – 7041;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 57946-63-1,Some common heterocyclic compound, 57946-63-1, name is 2-Bromo-4-(trifluoromethyl)aniline, molecular formula is C7H5BrF3N, 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 50-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of 2-bromo-4-(trifluoromethyl)benzenamine (1 g, 4.17 mmol, 1.00 equiv) in DMSO (20 mL), 4,4,5,5-tetramethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolane (1.58 g, 6.22 mmol, 1.50 equiv), PdCl2(dppf) (91 mg, 0.12 mmol, 0.03 equiv), potassium acetate (1 g, 10.40 mmol, 2.57 equiv). The resulting solution was stirred overnight at 80¡ã C. in an oil bath. The resulting mixture was combined with the solution of the previous batch and then diluted with 100 mL of ethyl acetate. The resulting mixture was washed with 2*100 mL of brine. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:100). This resulted in 1.2 g of 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4-(trifluoromethyl)benzenamine as a yellow solid.

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

Reference:
Patent; Ardelyx, Inc.; Lewis, Jason G.; Jacobs, Jeffrey W.; Reich, Nicholas; Leadbetter, Michael R.; Bell, Noah; Chang, Han-Ting; Chen, Tao; Navre, Marc; Charmot, Dominique; Carreras, Christopher; Labonte, Eric; (323 pag.)US9301951; (2016); B2;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 88223-35-2, These common heterocyclic compound, 88223-35-2, name is 2-Bromo-9,9-dibutyl-9H-fluorene, 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 benzoyl chloride (1.05 ml; 13.5 mmol), AlCl3 (2 g; 15 mmol) and2-bromo-9,9-dibutyl-9H-fluorene (4.0 g; 9.0 mmol) in CS2 (80 mL) was prepared and purged with argon. Themixture was stirred for 16 h under argon. After the solvent was evaporated, the aqueous layer was extractedwith DCM. The combined organic layer was washed with water and dried over MgSO4. The residue waspurified by column chromatography on silica gel (hexane : DCM = 1 : 1).Yield: white solid (415 mg; 9.0 mmol; 99 %).1H-NMR (300 MHz, DMSO-d6): delta 7.84-7.73 (m, 5H), 7.65-7.58 (m, 2H), 7.52-7.48 (m, 4H), 2.07-1.89 (m, 4H),1.16-1.03 (m, 4H), 0.68 (t, 6H), 0.66-0.54 (m, 4H).

Statistics shows that 2-Bromo-9,9-dibutyl-9H-fluorene is playing an increasingly important role. we look forward to future research findings about 88223-35-2.

Reference:
Article; Wada, Atsushi; Nishida, Jun-Ichi; Maitani, Masato M.; Wada, Yuji; Yamashita, Yoshiro; Chemistry Letters; vol. 43; 3; (2014); p. 296 – 298;,
Bromide – Wikipedia,
bromide – Wiktionary