Month: June 2021

Adding a certain compound to certain chemical reactions, such as: 24358-62-1, name is 1-(4-Bromophenyl)ethylamine, 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 24358-62-1, Formula: C8H10BrN

To a solution of 4-bromo-a-methylbenzylamine (1 .31 g, 6.57 mmol) and DIPEA (1 .72 mL, 9.85mmol) in anhydous THF (30 mL) was added 2-methoxybenzoyl chloride (1 .08 mL, 7.22 mmol) at 0 C. The reaction mixture was then allowed to return to room temperature and stirred overnight. The mixture was quenched with a saturated solution of ammonimum chloride (40 mL), extracted with EtOAc (3 chi 20 mL). The combined organic extracts were washed with water (2 chi 30 mL), brine (30 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure. Further purification by flash column chromatography (heptane/EtOAc 90:10 to 60:40) gave /V-[1 -(4-bromophenyl)ethyl]-2- methoxy-benzamide (2.07 g, 6.19 mmol, 94% yield) as a white solid. UPLC-MS (ES+, Short acidic): 1 .96 min, m/z 336.1 [M+2]+

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-(4-Bromophenyl)ethylamine, and friends who are interested can also refer to it.

Reference:
Patent; REDX PHARMA PLC; GUISOT, Nicolas; (191 pag.)WO2017/46604; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 65896-11-9, 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 65896-11-9 as follows.

Example 1A Methyl (2E)-3-[2-amino-3-fluorophenyl]propenoate Starting with 42.00 g (221.04 mmol) of 2-bromo-6-fluoroaniline, the general procedure [A] gives 29.66 g (68% of theory) of product. HPLC (method 1): Rt=4.14 min MS (ESI-pos): m/z=196 (M+H)+

According to the analysis of related databases, 65896-11-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Bayer HealthCare AG; US2007/281953; (2007); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 39478-78-9, name is 5-Bromo-2-methylaniline, 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 39478-78-9, Product Details of 39478-78-9

To a suspension [OF 5-BROMO-2-METHYLANILINE] (4.80g, 25.8 mmol) in concentrated [HCL] (16 mL) was added dropwise a solution of sodium nitrite (1.96 g, 28.4 mmol) in water (10 mL) over 30 minutes at [0C.] To the mixture was added dropwise a solution [OF SNCL2W2H2O] (17.46g, 77.4 mmol) in concentrated [HCL] (15 mL) over 50 minutes. After stirring for 1 hour at [0C,] the reaction mixture was basified with 50% NaOH (30 mL). The mixture was further diluted with water (20 mL) and treated with another [50% NAOH] (10 mL) and then crushed ice (100 g). The reaction mixture was extracted with ether (3 x 100 mL) and the combined organic phases were washed with brine, dried over [NA2SO4,] and filtered. The filtrate was acidified by adding an anhydrous solution of [HC1] in ether [(1] N in ether, 31 mL, 31 mmol). The precipitate was collected and dried under reduced pressure to give 4.57 g (75%) of title compound as a white amorphous solid. ‘H NMR (DMSO): 300MHz510. 31 (bs, 3H), 8.11 (bs, 1H), 7.12 (s, [IH),] 7.06 [(M,] 2H), 2.14 (s, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Bromo-2-methylaniline, and friends who are interested can also refer to it.

Reference:
Patent; WYETH; VIROPHARMA INCORPORATED; WO2003/99824; (2003); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 17247-58-4, name is (Bromomethyl)cyclobutane, 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 17247-58-4, SDS of cas: 17247-58-4

Blank magnesium chips (370 mg, 15.2 mmol) were covered with abs. THF (ca. 0.5 mL). Two drops283 (bromomethyl)cyclobutane (from 2.09 g, 14.0 mmol) were added. As the reaction started, the rest of284 the bromide was solved in abs. THF (4 mL) and the solution was added dropwise with stirring. After285 addition, the mixture was allowed to stand for 18 h at room temperature. The mixture was diluted286 abs. THF (10 mL), warmed near to reflux und slowly poured on crushed dry ice (100 mL). After287 warming up to about 0 C and addition of EtOAc (10 mL), the mixture was washed with 2 M HCl (10288 mL) and saturated with NaCl. The organic layer was separated and the aqueous layer was extracted289 with EtOAc (10 mL), the combined organic layers were dried over Na2SO4 and concentrated under290 reduced pressure resulting in 1.02 g cyclobutylacetic acid (7a) (64 %).

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:
Article; Durchschein, Christin; Bauer, Rudolf; Kretschmer, Nadine; Hufner, Antje; Rinner, Beate; Stallinger, Alexander; Deutsch, Alexander; Lohberger, Birgit; Molecules; vol. 23; 11; (2018);,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 10485-09-3,Some common heterocyclic compound, 10485-09-3, name is 2-Bromoindene, molecular formula is C9H7Br, 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.

Preparation of 2-Ethylindene 2-Bromoindene (8.1235 g, 0.04211 moles) and Ni(dppp)Cl2 (0.1536 g, 2.83*10-4 moles) were stirred in diethylether (100 mL) at -78 C. under a nitrogen atmosphere as ethylMgBr (0.045 moles, 15.00 mL of 3.0 M solution in diethylether) was added. The dry-ice bath was then removed and the reaction mixture allowed to warm to room temperature. The reaction mixture started off as a heterogeneous brick-red color and then turned to a homogeneous yellow/gold solution and then back to the heterogeneous brick-red mixture during the course of the warm-up. Gas chromatographic analysis after 2 hours of stirring at room temperature showed that the reaction was substantially quantitative. After the reaction period the mixture was poured onto ice and then extracted with 1 M HCL (1*100 mL) and 1 M NaHCO3 (1*100 mL) and then dried with MgSO4 and filtered. The desired product was isolated as a light yellow oil (5.65 g, 93.1 percent). 1 H NMR (300 MHz, CDCl3, TMS): delta1.31 (t, 3 JHH =7.4 Hz, 3H), 2.59 (q, 3 JHH =7.4 Hz, 2H), 3.39 (s, 2H), 6.59 (s, 1H), 7.16-7.38 (m, 3H), 7.46 (d, 3 JHH =7.4 Hz, 1H). 13 C NMR (75 MHz, CDCl3): delta13.65, 24.63, 41.23, 119.96, 123.47, 123.60, 125.25, 126.29, 143.12, 145.76, 152.47. GC-MS: Calculated for C11 H12 144.22, found 144.10.

The synthetic route of 10485-09-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; The Dow Chemical Company; US6015868; (2000); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 626-40-4, 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. 626-40-4 name is 3,5-Dibromoaniline, 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.

Compound II (2.25 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 then warmed at reflux under nitrogen until the reaction was completeOften 5 hours). The reaction mixture was carefully poured into 200 mL of ice water, stirred and extracted with 50 mL × 3 CH 2 Cl 2. The combined extracts were driedWashed sequentially with 1% dilute hydrochloric acid (200 mL) and brine (100 mL) and dried over anhydrous sodium sulfate. Remove the desiccant by suction filtrationEvaporation on a rotary evaporator gave Compound IV as a white solid

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

Reference:
Patent; Guangdong Sai Bo Technology Co., Ltd.; Guo Huijun; (9 pag.)CN106831837; (2017); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 327-52-6, name is 1-Bromo-2,4,5-trifluorobenzene, 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 327-52-6, Quality Control of 1-Bromo-2,4,5-trifluorobenzene

Into a 100 mL three-necked flask were added 4.62 g 1-bromo-2,4,5-trifluorobenzene (0.022 mol) and anhydrous tetrahydrofuran (50 mL). The resulting mixture was cooled to -20 C. The solution of isopropylmagnesium bromide (22 mmol) in tetrahydrofuran (22 ml, 1M THF) was slowly added dropwise under nitrogen. After the addition was complete, the reactants were maintained at -20 C. for later use. Cuprous bromide-dimethyl sulfide (0.41 g, 0.002 mol) was suspended in 5 ml anhydrous tetrahydrofuran. The resulting mixture was cooled to -5 C. The Grignard reagent as described above was slowly added dropwise under nitrogen. After 15 min, a solution of the aziridine compound as shown in the above reaction formula (4.16 g, 0.015 mol) in 30 mL tetrahydrofuran was slowly added dropwise. After additional 5 min, 50 mL saturated solution of ammonia chloride was added to quench the reaction. Into this obtained solution was added 50 mL ethyl acetate. The separated water layer was extracted with another 50 mL ethyl acetate. The obtained organic layers were collected together and further washed with saturated solution of sodium chloride and then dried over anhydrous sodium sulfate, followed by filtration and concentration to obtain a crude product, which was further treated by column chromatography to obtain a compound (4.08 g, 0.0116 mol, yield 77%). 1H NMR (400 MHz, CDCl3) delta7.537.22 (m, 10H), 7.05 (t, J=10.5 Hz, 1H), 6.93 (t, J=10.7 Hz, 1H), 5.12 (d, J=12.6 Hz, 1H), 3.973.85 (m, 1H), 3.82 (d, J=6.2 Hz, 1H), 3.773.55 (m, 1H), 3.62 (s, 2H), 3.51 (s, 2H), 2.82 (s, 2H), 1.871.68 (m, 1H), 1.631.48 (m, 1H). Ms (M++1): 400.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-2,4,5-trifluorobenzene, and friends who are interested can also refer to it.

Reference:
Patent; ZHEJIANG HISOAR PHARMACEUTICAL CO., LTD.; Pan, Xianhua; Li, Weijin; Zhang, Qunhui; Ruan, Libo; Yu, Wansheng; Deng, Fei; Ma, Tianhua; Huang, Mingwang; He, Minhuan; US2013/281695; (2013); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 18599-22-9, name is 4-Bromo-3,3,4,4-tetrafluorobut-1-ene, molecular formula is C4H3BrF4, 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. Application In Synthesis of 4-Bromo-3,3,4,4-tetrafluorobut-1-ene

General procedure: In a two-necked round-bottomed flask, equipped with a teflon-coated stirrer bar and reflux condenser, was added ethyl 2-iodobenzoate (3j, 0.14 g 0.50 mmol), Cu2O (0.060 g, 0.42 mmol), and a DMF solution of 2-Zn (0.65 M, 1.54 mL, 1.0 mmol), and the mixture was stirred at 100 C for 24 h. After being cooled to room temperature, the resulting solution was subjected to a short pad of silica gel using hexanes as an eluent. The filtrate was concentrated in vacuo to give the crude materials, which was purified by silica gel column chromatography to provide the corresponding compound 4j (0.13 g, 0.48 mmol) in 96% yield as an yellow oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 18599-22-9, its application will become more common.

Reference:
Article; Tamamoto, Ken; Yamada, Shigeyuki; Konno, Tsutomu; Beilstein Journal of Organic Chemistry; vol. 14; (2018); p. 2375 – 2383;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 16518-62-0,Some common heterocyclic compound, 16518-62-0, name is 3-Bromo-N,N-dimethylaniline, molecular formula is C8H10BrN, 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 mixture ofpalladium(ll) acetate (3 mg, 5 molpercent), 2-dicyciohexylphosphino-2′-(A/,A/-dimethylamino)biphenyl (10 mg, 5 molpercent) and lithium bis(trimethylsilyl)amide(0.55 rnl_, 0.55 mmol, 1.1 equiv, 1.0 M solution in tetrahydrofuran) in toluene(0.5 ml) under nitrogen at-10 °C, was added a solution of 3-[5-(3,4-dichloro-10 phenyl)-1 -(2,4-dichloro-phenyl)-1 H-pyrazol-3-yl]-propionic acid tert-butyl ester(243 mg, 0.50 mmol, 1.0 equiv) in toluene (1.0 mL). This mixture was stirred at-10 °C for 10 min, then (3-bromo-phenyl)-dirnethyl-arnine (42 mg, 0.21 mmol,0.45 equiv) in toluene (0.5 ml) was added. The resulting solution was allowedto warm to room temperature then was heated to 80 °C for 3 h. The reaction15 mixture was cooled to room temperature, and the reaction was quenched withsatd aq ammonium chloride (1.0 ml). Water (10.0 ml) was added, and theresulting mixture was extracted with diethyl ether (2×10 ml). The combinedextracts were washed with brine (10 ml), dried (Na2SC>4), and concentratedunder reduced pressure. The crude material was purified by reversed-phase20 HPLC to afford the desired aryl acetic acid ester (20 mg, 16percent). MS (ESI):mass calculated for CaohbCUNaC^, 603.10; m/z found, 604.1 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Bromo-N,N-dimethylaniline, its application will become more common.

Reference:
Patent; JANSSEN PHARMACEUTICA N.V.; WO2005/5393; (2005); A2;,
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. 39478-78-9, name is 5-Bromo-2-methylaniline, A new synthetic method of this compound is introduced below., HPLC of Formula: C7H8BrN

General procedure: Under N2 atmosphere, a mixture of intermediate 12 (263.5 mg,1.0 mmol), 3-bromoaniline (172.0 mg, 1.0 mmol), Cs2CO3 (325.8 mg,1.0 mmol), Pd2(dba)3 (45.8 mg, 0.05 mmol) and Davephos (31.5 mg,0.08 mmol) in MeCN (6.0 ml) was heated to reflux for 5 h. The reactionmixture was cooled to room temperature and diluted withethyl acetate. The resulting mixturewas filtered off and the solutionwas concentrated under vacuum to give a crude product 16 thatwas purified by column chromatography on silica using a solvent of10% ethyl acetate in hexanes. The desired compound 16 was obtainedas a yellow solid (220.0 mg, yield 72%). For the synthesis ofintermediate 13-15, compound 12 or commercially available 11and corresponding aromatic amine were used respectivelyfollowing the procedure described for 16.

The synthetic route of 39478-78-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yu, Jiang; Zhang, Lanxi; Yan, Guoyi; Zhou, Peiting; Cao, Chaoguo; Zhou, Fei; Li, Xinghai; Chen, Yuanwei; European Journal of Medicinal Chemistry; vol. 171; (2019); p. 265 – 281;,
Bromide – Wikipedia,
bromide – Wiktionary