Category: bromides-buliding-blocks

Adding a certain compound to certain chemical reactions, such as: 3814-30-0, name is (Bromomethyl)cyclopentane, belongs to bromides-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 3814-30-0, Quality Control of (Bromomethyl)cyclopentane

To a solution of 20.6 g (0.1 mol) of 4-(3,5-difluorophenyl)phenol in 200 mL of N,N-dimethylformamide in a 500 mL of three-necked flask, 4.8 g (0.12 mol) of 60% sodium hydride was added portionwise under nitrogen with stirring at 30 C., and then 16.3 g (0.1 mol) of cyclopentyl methyl bromide was added dropwise. After the reaction was stuffed for 20 hours, it was poured into 500 mL of water, and was extracted with hot petroleum ether (200 mL¡Á2). The combined organic phases was washed with water to neutral, and the solvent was then distilled off under reduced pressure. 15 g of 4-a as white crystals was obtained by recrystallization from ethanol. GC purity: 98.9%.

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, (Bromomethyl)cyclopentane, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Shijiazhuang Chengzhi Yonghua Display Materials Co.,Ltd.,; Yun, Kuol Liang; Liang, Jian; Wang, Kwei; Hua, RuiMao; Wen, Kang; Jang, Fang Miao; Meng, Jin Song; (30 pag.)KR101530834; (2015); B1;,
Bromide – Wikipedia,
bromide – Wiktionary

These common heterocyclic compound, 591-19-5, name is 3-Bromoaniline, 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. SDS of cas: 591-19-5

In the preparation method of the trifluoromethyl aromatic amine of the present embodiment, the aromatic amine is m-bromoaniline, and the other reactions and post-treatment processes are the same as those in Example 28, and three kinds of trifluoromethyl aromatic amine products are obtained. The preparation method of the trifluoromethyl aromatic amine of the present embodiment, the aromatic amine is aniline, and the nickel compound is nickel hydroxide.The base is potassium carbonate, and the reaction process parameters are: 1-trifluoromethyl-1,2-phenyliodo-3(H)-one (0.5 mmol, 1.0 eq).Aromatic amine (1.5 mmol, 3.0 eq), nickel hydroxide 10 mol%, potassium carbonate (1.5 mmol, 3.0 eq),DMSO (2 mL) was reacted at 35 C for 2 h, and the other reactions and workup procedures were the same as in Example 1.

The synthetic route of 3-Bromoaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zhengzhou Taijihongnuo Pharmaceutical Co., Ltd.; Wu Yusheng; Gao Xianying; Geng Yang; Han Shuaijun; Liang Apeng; Li Jingya; Zou Dapeng; Wu Yangjie; (19 pag.)CN108503552; (2018); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 65896-11-9, These common heterocyclic compound, 65896-11-9, name is 2-Bromo-6-fluoroaniline, 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.

Stage 1: N-[1-(2-Bromo-6-fluorophenyl)-1H-1,2,4-triazol-3-yl]benzamide Ethyl [5-phenyl-1,2,4-oxadiazol-3-yl]imidoformate (2.00 g) and 2-bromo-6-fluoroaniline were heated to 150 C. for 4 h, the reaction mixture was cooled down to room temperature, the residue was stirred with 20 ml of ethanol for 45 minutes and the remaining solids were filtered off with suction. This left 2.0 g of the desired title compound. HPLC-MS: log P (neutral)=1.79; mass (m/z): 361 (M+H)+; 1H NMR (DMSO-D6) 7.587 (m, 2H), 7.638 (m, 3H), 7.768 (m, 1H), 8.002 (m, 2H), 8.891 (s, 1H), 11.053 (s, 1H).

Statistics shows that 2-Bromo-6-fluoroaniline is playing an increasingly important role. we look forward to future research findings about 65896-11-9.

Reference:
Patent; BAYER CROPSCIENCE AKTIENGESELLSCHAFT; HEILMANN, Eike Kevin; WROBLOWSKY, Heinz-Juergen; TRAUTWEIN, Axel; GREUL, Joerg; DEMBSKI, Hardwin; ILG, Kerstin; PORTZ, Daniela; GOERGENS, Ulrich; (85 pag.)US2017/73318; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 59907-13-0, 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 59907-13-0 as follows.

General procedure: To a mixture of the appropriate amine E (1 eq), the appropriate halide (1.05 to 1.2 eq) and sodium ferf-butoxide (2 eq) in toluene (3 mL/mmol) under N , was added BINAP (0.2 eq) and Pd2(dba)3 (0.1 eq). The rxn mixture was flushed with N , heated to a given temperature in a sealed vial and stirred for a given time (see Table 27). It was partitioned between water and EtOAc and the org. phase was washed with brine, dried over MgSCh and concentrated in vacuo. The crude was purified by CC using Hept/EtOAc.

According to the analysis of related databases, 59907-13-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; IDORSIA PHARMACEUTICALS LTD; FROIDEVAUX, Sylvie; HUBLER, Francis; MURPHY, Mark; RENNEBERG, Dorte; STAMM, Simon; (266 pag.)WO2019/137927; (2019); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

72678-19-4, name is 2,6-Dibromo-4-(trifluoromethyl)aniline, belongs to bromides-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. Quality Control of 2,6-Dibromo-4-(trifluoromethyl)aniline

General procedure: A suspension of potassium hydride (3 equiv) in THF (0.6 M) was cooled in an ice-water bath. A solution of sulfonamide, sulfonamide or aniline (1.0 equiv) in THF (0.20 M) was added dropwise, and the suspension was stirred for 15 min. 1,1′-Carbonyldiimidazole (1.0 equiv) was dissolved in 1:1 THF/dioxane (0.20 M) and added dropwise to the reaction mixture, resulting in the formation of a white precipitate. The ice-water bath was removed, and the reaction mixture was allowed to warm to ambient temperature and was stirred for 2 h. A solution of diamine S-1 (1.0 equiv) in THF (1.0 M) was added dropwise, and the suspension was stirred at room temperature for 20 h. The reaction was quenched with a solution of acetic acid (3 equiv) in THF (1.0 M). The crude product was concentrated in vacuo and purified by silica gel chromatography.

The synthetic route of 72678-19-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kimmel, Kyle L.; Robak, Maryann T.; Thomas, Stephen; Lee, Melissa; Ellman, Jonathan A.; Tetrahedron; vol. 68; 12; (2012); p. 2704 – 2712;,
Bromide – Wikipedia,
bromide – Wiktionary

These common heterocyclic compound, 1003-98-1, name is 2-Bromo-4-fluoroaniline, 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. Safety of 2-Bromo-4-fluoroaniline

The title compound was prepared by a modified procedure reported in the literature (Org. Lett., 2014, 16, 2916-2919). A mixture of 2-bromo-4-fluoroaniline (20 g, 105 mmol), PdCl2(PPh3)2 (7.39 g, 10.53 mmol), 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (40.4 g, 316 mmol) and Et3N (58.7 mL, 421 mmol) in dioxane (400 mL) was stirred at 110C for 16 h under nitrogen atmosphere. It was cooled to rt and poured into a saturated aqueous solution of ammonium chloride (300 mL). The mixture was extracted with DCM (300 mL). The organic layer was separated, dried over sodium sulfate, and filtered. The filtrate was concentrated and the residue was purified by flash column chromatography on silica gel (eluting with EtOAc/petroleum ether = 10: 90 v/v) to give the title compound.1H NMR (400 MHz, CDCl3): delta 7.25 (m, 1H), 6.92 (m, 1H), 6.54 (m, 1H), 4.42 (brs, 2H), 1.34 (s, 12H).

The synthetic route of 2-Bromo-4-fluoroaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; XU, Jiayi; ALI, Amjad; ZHOU, Wei; GAO, Ying-Duo; EDMONDSON, Scott, D.; MERTZ, Eric; NEELAMKAVIL, Santhosh, F.; LIU, Weiguo; SUN, Wanying; SHEN, Dong-Ming; HARPER, Bart; ZHU, Cheng; BARA, Thomas; LIM, Yeon-Hee; YANG, Meng; (227 pag.)WO2017/74832; (2017); 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. 583-70-0, name is 2,4-Dimethylbromobenzene, A new synthetic method of this compound is introduced below., Recommanded Product: 583-70-0

General procedure: To a flask containing Mg turnings (0.29 g, 12 mmol) was added1-bromo-4-methylbenzene (1.37 g, 8.0 mmol) in THF (8 mL) at room temperature. After being stirred for 2 h, DMF (1.3 mL,12 mmol) was added to the reaction mixture. The obtained mixturewas stirred for 2 h at 0 C. Then, aq NH3 (7 mL, 28-30%) and I2 (4.06 g, 16 mmol) were added to the reaction mixture. After beingstirred for 2 h at room temperature, the reaction mixture waspoured into satd aq Na2SO3 solution and was extracted with CHCl3 (3*30 mL). The organic layer was dried over Na2SO4 and filtered.After removal of the solvent, the residue was purified by shortcolumn chromatography on silica gel (eluent: hexane/ethylacetate=9:1, v/v) to provide pure 4-methyl-1-benzonitrile (0.77 g) in 82% yield.

The synthetic route of 583-70-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ishii, Genki; Harigae, Ryo; Moriyama, Katsuhiko; Togo, Hideo; Tetrahedron; vol. 69; 5; (2013); p. 1462 – 1469;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 68322-84-9,Some common heterocyclic compound, 68322-84-9, name is 2-Bromo-1-fluoro-4-(trifluoromethyl)benzene, molecular formula is C7H3BrF4, 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.

Cul (150 mg, 0.79 mmol) and N,/V-dimethylethylenediamine (0.17 mL, 1.58 mmol) were added to a mixture of 3-bromo-4-fluorobenzotrifluoride (768 mg, 3.16 mmol), intermediate 21 (250 mg, 0.79 mmol), and Cs2C03 (644 mg, 1.98 mmol) in DMF (3 mL). The r.m. was heated at 170 C for 90 min twice, the r.m. was cooled, EtOAc was added and the mixure was washed with a IM aq. H4OH solution, water and brine. The organic layer was dried (MgS04), filtered and the solvent was evaporated in vacuo. The residue was purified by flash column chromatography (eluent: DCM/MeOH from 100/0 to 97/3). The product fractions were collected and concentrated in vacuo. Then the residue was repurified by RP preparative HPLC [RP Vydac Denali C18 – IotaOmicronmu?iota, 250 g, 5cm); mobile phase: a gradient of (0.25% H4HC03 sol. in water)/CH3CN)]. The product fractions were collected and concentrated in vacuo. Yield: 75 mg of compound 14 (20 %).

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-1-fluoro-4-(trifluoromethyl)benzene, its application will become more common.

Reference:
Patent; JANSSEN PHARMACEUTICALS, INC.; BISCHOFF, Francois, Paul; VELTER, Adriana, Ingrid; VAN BRANDT, Sven, Franciscus, Anna; BERTHELOT, Didier, Jean-Claude; WO2012/126984; (2012); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

58971-11-2, name is 3-Bromophenethylamine, belongs to bromides-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. SDS of cas: 58971-11-2

To a cooled (ice bath) solution of 3-bromophenethylamine (21 g, 105 mmol) and TEA (12.7 g, 125 mmol) in DCM (150 mL) was added dropwise trifluoroaceticanhydride (24 g, 115 mmol). The reaction was stirred at room temperature for18 h then poured into water (200 mL) and extracted with DCM (2 x 200 mL). The combined organic layers were concentrated then diluted with methyl tert-butyl ether (TBME) (250 mL) and H20 (50 mL). The layers were separated and the organic phase was washed with brine (50 mL) then dried over Na2504,filtered and concentrated to give crude N-(3-bromophenethyl)-O-(2,2,2-trifluoro- acetyl) hydroxylamine (33 g, >100%) as a brown solid. 1H NMR (400 MHz, DMSO-d6) O [ppm] 9.49 (br 5, 1H), 7.47- 7.35 (m, 2H), 7.30- 7.17 (m, 2H), 3.42 (d, J=4.0 Hz, 2H), 2.80 (t, J=7.0 Hz, 2H).

The synthetic route of 58971-11-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; ITEOS THERAPEUTICS; NINKOVIC, Sacha; CROSIGNANI, Stefano; SCALES, Stephanie Anne; MCALPINE, Indrawan James; COLLINS, Michael Raymond; MADERNA, Andreas; WYTHES, Martin; (295 pag.)WO2016/147144; (2016); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 454-79-5, name is 2-Bromo-5-(trifluoromethyl)aniline, belongs to bromides-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 454-79-5, name: 2-Bromo-5-(trifluoromethyl)aniline

Example 20-1: General procedure for Stille coupling, exemplified by synthesis of compound 2-Pyridin-2-yl-5-trifluoromethyl-phenylamine (108).; A screw cap tube was charged with 2-tributyltinpyridine (1.4 eq), prepared from 2- bromopyridine and tributyltin hydride according to the procedure described in example 19-1, o-bromoaniline (200 mg, 1 eq), Pd(dba)2 (10-14 mg, 2 mol%), CuI (20 mg, 10 mol%), and PPh3 (40 mg, 15 mol%). The mixture was degassed and back-filled with argon. Dry diethyl ether (5 ml) was added, and the reaction mixture was heated at 120C for 4h in a microwave oven. The reaction mixture was cooled to room temperature, stirred with saturated aqueous KF (3 ml) for 3h, and filtered. The solid was discarded after washing with ethyl acetate (three times). The liquid was poured into H2O and extracted with ethyl acetate. The combined organic layer was washed with H2O and brine, dried over MgSO4, and filtered and the solvent was removed in vacuo. The residue was purified by column chromatography on silica (ethyl acetate/petroleum ether as eluent) to afford the title compound as a white solid (60 mg, 38%). M+ 239.

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; TIBOTEC PHARMACEUTICALS LTD.; MEDIVIR AB; WO2007/14922; (2007); A1;,
Bromide – Wikipedia,
bromide – Wiktionary