Author: Jessica.F

Synthetic Route of 626-40-4, 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 626-40-4 as follows.

Compound II (2.52 g, 10 mmol), compound III (2.51 g, 10 mmol) and diisopropylethylamine (DIPEA,3.88 g, 30 mmol) was dissolved in 50 mL of dry xylene and refluxed under nitrogen atmosphere until the reaction was completeUsually 5 hours). The reaction mixture was carefully poured into 200 mL of ice water, stirred, extracted with 50 mL of X3CH2C12, the combined phases were combined,Washed successively with 1% dilute hydrochloric acid (200 mL) and brine (100 mL), and dried over anhydrous sodium sulfate. The desiccant was removed by suction filtrationEvaporated on a rotary evaporator to give compound IV, a white solid.

According to the analysis of related databases, 626-40-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Guangdong Sai Bo Technology Co., Ltd.; Guo Huijun; (11 pag.)CN106831835; (2017); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 6274-57-3, These common heterocyclic compound, 6274-57-3, name is 1-(4-Bromophenyl)-N,N-dimethylmethanamine, 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.

Magnesium strips (0.36 g, 15 mmol), a small amount of iodine, 4-bromo-N,N-dimethylbenzylamine (0.21 g, 1 mmol), tetrahydrofuran (25 mL) were added to a round bottom flask, and the mixture was heated to reflux. The reaction is initiated.A solution of 4-bromo-N,N-dimethylbenzylamine (2.98 g, 14 mmol) in THF (5 mL) was then added dropwise over 30 min.After the addition is completed, the reflux is continued for 2 hours.Then cooled to room temperature, and slowly added the compound a derived from amino acid within 30 min.(2-[(tert-Butoxycarbonyl)amino]-3-phenylpropanoic acid methyl ester) (1.40 g, 5 mmol) in THF (5 mL)The saturated ammonium chloride solution was quenched, extracted with ethyl acetate and washed with saturated brine.After drying over anhydrous sodium sulfate, a crude Boc-protected amino alcohol b was obtained, which was used directly in the next step.

The synthetic route of 6274-57-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; University of Science and Technology of China; Wang Zhiyong; Gui Yang; (28 pag.)CN108821995; (2018); A;,
Bromide – Wikipedia,
bromide – Wiktionary

57946-63-1, name is 2-Bromo-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. Computed Properties of C7H5BrF3N

Reference Example 57 4-[2-{[2-Bromo-4-(trifluoromethyl)phenyl]amino}-4-chloro-7-(1-ethylpropyl)-1H-benzimidazol-1-yl]butan-1-ol A mixture of ethyl 4-[2,4-dichloro-7-(1-ethylpropyl)-1H-benzimidazol-1-yl]butanoate (Reference Example 33; 2.24 g, 6.63 mmol), 2-bromo-4-trifluoromethylaniline (3.18 g, 13.25 mmol), p-toluenesulfonic acid monohydrate (1.35 g, 7.09 mmol) and xylene (5.0 mL) was stirred at 130° C. for 15 hr. After cooling, the reaction mixture was neutralized with aqueous saturated sodium hydrogen carbonate and extracted with ethyl acetate (*3). The combined organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography eluding with a 0-15percent ethyl acetate/n-hexane gradient mixture to give crude ethyl 4-[2-{[2-bromo-4-(trifluoromethyl)phenyl]amino}-4-chloro-7-(1-ethylpropyl)-1H-benzimidazol-1-yl]butanoate. The crude material (MS Calcd.: 573; Found: 574 (M+H)) was subjected for the next step without further purification.

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

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; US2009/186879; (2009); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

1559-88-2, name is 3-Bromo-1,2,4,5-tetrafluorobenzene, 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. Recommanded Product: 1559-88-2

(0131) To a 100 mL flame-dried flask was added 308 (0.224 g, 0.300 mmol, 1 equiv) and [1, 1?bis(diphenylphosphino)ferrocenedichloropalladium (0.022, 0.030 mmol, 0.100 equiv). After the solids were added, the flask was evacuated and backfilled with nitrogen 5 times. 1,4-dioxane (8.0 mL) was then added to the flask, followed by 1-bromo-2,3,5,6-tetrafluorobenzene (0.412 g, 1.80 mmol, 6 equiv), and the solution was sparged for 10 min. before 2M K3PO4 (0.825 mL, 1.65 mmol, 5.5 equiv), sparged for 1 h prior to use, was added. The solution was then placed in an 80 C. oil bath and allowed to stir overnight. The next day, the black solution was allowed to come to room temperature before removing the solvent under reduced pressure. (0132) Next, H2O (50 mL) was added, followed by extraction with hexanes (3×50 mL). The combined organic phases were then washed with water (3×50 mL), brine (1×75 mL), and dried over sodium sulfate. After removing the solvent via rotary evaporation, the crude, yellow-orange oil was purified via column chromatography (2-5% EtOAc/Hexanes) and 310 isolated as a pale yellow oil (0.175 g, 74%). 1H NMR (500 MHz, Chloroform-d) delta 7.47 (d, J=7.7 Hz, 2H), 7.37 (d, J=7.9 Hz, 2H), 7.04 (p, J=8.4 Hz, 2H), 6.07 (s, 4H), 0.96 (t, J=7.9 Hz, 18H), 0.64 (q, J=7.8 Hz, 12H). 13C NMR (126 MHz, Chloroform-d) delta 146.95, 131.58, 129.94, 126.12, 71.38, 7.03, 6.46. 19F NMR (471 MHz, Chloroform-d) delta -139.24 (m, J=22.4, 11.3 Hz), -143.81 (m, J=21.1, 12.7, 7.4 Hz).

The synthetic route of 1559-88-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; University of Oregon; Jasti, Ramesh; Van Raden, Jeff; Leonhardt, Erik; US2018/290952; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 583-75-5, name is 4-Bromo-2-methylaniline, This compound has unique chemical properties. The synthetic route is as follows., name: 4-Bromo-2-methylaniline

Preparation #4: 2-Methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenylamine A mixture of 4-bromo-2-methylaniline (0.250 g, 1.34 mmol), bis(pinacolato)diboron (0.442 g, 1.747 mmol), dichloro[1,1’bis(diphenylphosphino)-ferrocene]palladium (II) dichloromethane adduct (0.110 g, 0.134 mmol), and potassium acetate (0.329 g, 3.357 mmol) was heated in N,N-dimethylformamide (5 mL) at about 80 C. for about 15 h under an atmosphere of nitrogen. The mixture was allowed to cool to ambient temperature and was purified by flash column chromatography on silica gel using ethyl acetate/heptane (3:7) as the mobile phase to give 2-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenylamine as a yellow oil (0.213 g, 0.914 mmol); RP-HPLC (25% to 100% acetonitrile/0.1 M aqueous ammonium acetate, buffered to pH 4.5, over 10 min at 1.0 mL/min; lambda=254 nm; Hypersil C18, 100 A, 5 mum, 250*4.6 mm column) Rt 11.02 min.

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 583-75-5.

Reference:
Patent; Wishart, Neil; Friedman, Michael; Arnold, Lee D.; Yang, Bryant; Fix-Stenzel, Shannon R.; Ericsson, Anna; Michaelides, Michael R.; Qian, Xiao-Dong; Holms, James H.; Steinman, Douglas H.; Tian, Zhengping; Wittenberger, Steven J.; US2006/25383; (2006); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 5279-32-3, 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. 5279-32-3 name is 5,6-Dibromobenzo[d][1,3]dioxole, 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.

Method B: 4-Amino-1-(4-methoxybenzyl)-1H-imidazo[4,5-c]pyridine-2-thiol (100 mg, 0.349 mmol), 5,6-dibromo-1,3-benzodioxole (196 mg, 0.698 mmol), Pd2dba3 (16 mg, 1.8×10-2 mmol), Xantphos (21 mg, 3.5×10-2 mmol), and Cs2CO3 (227 mg, 0.698 mmol) were placed in a vial and degassed dioxane (1.2 mL) was added to the mixture. After heating at 100 C. for 10 h, the mixture was diluted with EA, washed with brine, dried (Na2SO4), filtered, and concentrated in vacuum. The residue was purified by column chromatography (SiO2, MeOH/CH2Cl2, 0 to 10%) to afford the title compound (54 mg, 31%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5,6-Dibromobenzo[d][1,3]dioxole, and friends who are interested can also refer to it.

Reference:
Patent; Myrexis, Inc.; US8017780; (2011); B1;,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 608-30-0, name is 2,6-Dibromoaniline, molecular formula is C6H5Br2N, 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. Computed Properties of C6H5Br2N

A solution of 2,6-dibromoaniline (1.0 g, 4.0 mmol) in CHCl3 (8 ml) was treated with a suspension of m-CPBA (2.1 g, 12.0 mmol) in CHCl3 (8 ml) and the resulting mixture stirred overnight. After 24 h the solution was diluted with CHCI3 and washed successively with sat. aq. Na2S2Os, sat. aq. NaHCO3 and brine. The organic layers were dried over Na2SO4, filtered, concentrated and dried in vacuo to afford 1,3-dibromo-2-nitrosobenzene (1.0 g, 100 %); the resultant solid was used directly in the next stage.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 608-30-0, its application will become more common.

Reference:
Patent; UNIVERSITY OF DURHAM; WO2009/34396; (2009); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 327-51-5, name is 1,4-Dibromo-2,5-difluorobenzene, molecular formula is C6H2Br2F2, 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. Formula: C6H2Br2F2

A solution of 1,4-dibromo-2,5-difluorobenzene (640 mg, 2.35 mmol) in dry diethyl ether (10 mL) cooled in a dry ice-acetone bath was treated dropwise with 2.5 M n-butyllithium in hexanes (1.04 mL, 2.59 mmol). The resulting solution was stirred at -78 C. for 30 min, then was treated with a piece of dry ice. The cooling bath was removed after 5 min and the mixture was stirred for another 30 min while warming to room temperature. The mixture was diluted with EtOAc and water. The organic phase was separated and washed twice with saturated aqueous NaHCO3. The combined aqueous phases were acidified with 1 M aqueous HCl, extracted twice with DCM, and the combined organic phases were dried and concentrated to give 4-bromo-2,5-difluorobenzoic acid as a white solid (297 mg, 53% yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 327-51-5, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; Liu, Qingjie; Watterson, Scott Hunter; Batt, Douglas G.; Ahmad, Saleem; Beaudoin Bertrand, Myra; Gong, Hua; Guo, Weiwei; Macor, John E.; Ngu, Khehyong; Tebben, Andrew J.; Tino, Joseph A.; (177 pag.)US2016/115126; (2016); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 955959-84-9, name is 4-(4-Bromophenyl)dibenzo[b,d]furan belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 4-(4-Bromophenyl)dibenzo[b,d]furan

In a round bottom flask, Intermediate M-1 10g (30.9mmol) andintermediate compound M-5 9.6g (37.08mmol),sodium t-butoxide 5.35g (55.6mmol) dissolved in 155 mL toluene was added. Pd(dba) 2 0.178g (0.31mmol) and tri-tert-butylphosphine0.125g (0.62mmol) were added in order and the mixture was stirred under refluxfor 4 hours under a nitrogen atmosphere. After completion of the reaction, thereaction mixture was extracted with toluene, the organic layer was dried anddistilled over magnesium sulfate, filtered and the filtrate was concentratedunder reduced pressure. The product was subjected to silica gel columnchromatography using n- hexane / dichloromethane (7: 3 by volume) to give thetarget intermediate M-7 11.2 g (72%yield) as a white solid.

The synthetic route of 955959-84-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CHEIL INDUSTRIES CO., LTD; RYU, DONG WAN; JO, YOUNG GYUNG; JONG, SONG HYUN; SHIN, CHANG JU; LEE, HAN IR; KANG, UI SOO; KIM, CHANG WOO; PARK, MIN JI; YU, UHN SON; JO, PYUNG SOK; (73 pag.)KR2015/130221; (2015); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 460-00-4,Some common heterocyclic compound, 460-00-4, name is 1-Bromo-4-fluorobenzene, molecular formula is C6H4BrF, 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.

Carbazole (5.03 g, 30.1 mmol), 1-Fluoro-4-bromobenzene (14.0 mL, 127 mmol) and Cs2CO3 (39.9 g, 122 mmol) were added to 100 mL of DMF under nitrogen gas, and the mixture was stirred at room temperature for 16 hours. After the reaction mixture was cooled to room temperature and filtered under reduced pressure, the filtrate was washed with distilled water (100 mL X 3) and extracted with EtOAc (100 mL X 3). The organic layer was dried with MgSO 4, filtered under reduced pressure, and the solvent was removed. The reaction mixture was separated by Silica column chromatography (Hexanes ? Hexane: DCM (dichloromethane) = 1: 1) and recrystallized with DCM / MeOH to give 6.42 g (yield: 66%) of pure compound 1-3.

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

Reference:
Patent; LG Display Co., Ltd.; Yoon Dae-w; Seo Bo-min; Ryu Mi-sang; Kim Chun-gi; (39 pag.)KR2019/68072; (2019); A;,
Bromide – Wikipedia,
bromide – Wiktionary