Tag: M.W=200-300

Synthetic Route of 60956-23-2,Some common heterocyclic compound, 60956-23-2, name is 1,2-Dibromo-4-methylbenzene, molecular formula is C7H6Br2, 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.

General procedure: A 12 mL vial was charged with Pd(OAc)2 (2 mol%), BuPAd2 (6 mol%), and a stirring bar. Then, 2 ml dioxane and 1 mmol of bromobenzene were injected by syringe. The vial (or several vials) was placed in an alloy plate, which was transferred into a 300 mL autoclave of the 4560 series from Parr Instruments under argon atmosphere. After flushing the autoclave three times with NH3, a pressure of 2 bar NH3 and 2 bar CO was adjusted at ambient temperature. Then, the reaction was performed for 16 hours at 100 oC. After the reaction is finished, the autoclave was cooled down to room temperature and the pressure was released carefully. Then, CuI (5 mol%), DMEDA (10%), K2CO3 (3 mmol) and 1,2-dibromobenzene were added in under air, the vial was closed and heated to 110oC for 20 hours. The reaction mixture cooled down to room temperature. The solution was extracted 3-5 times with 2-3 ml of ethyl acetate from aqua solution. After evaporation of the organic solvent the residue was adsorbed on silica gel and the crude product was purified by column chromatography using n-heptane/AcOEt (20:1) as eluent.

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

Reference:
Article; Wu, Xiao-Feng; Neumann, Helfried; Neumann, Stephan; Beller, Matthias; Tetrahedron Letters; vol. 54; 24; (2013); p. 3040 – 3042;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 327-51-5, 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 327-51-5 as follows.

1,4-Dibromo-2,5-difluorobenzene, 4-methoxycarbonylphenylboronic acid, potassium carbonate and tetrakis (triphenylphosphine) palladium were placed in a reaction In the reactor, and ethylene glycol dimethyl ether was added to the reactor, Then under the protection of nitrogen at 85 C for 36h after the first reaction A reaction solution, after the first reaction solution is cooled, The first reaction solution was poured into water and extracted with dichloromethane, and then ethylene glycol dimethyl ether was removed, The remaining material after pumping away ethylene glycol dimethyl ether, separated and purified by silica gel column chromatography to give To the intermediate product 2 ‘, 5′-difluoro- [1,1’: 4 ‘, 1 “-terphenyl] -4,4” -dimethyl ester;

According to the analysis of related databases, 327-51-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Guangdong University of Technology; He Jun; Huang Jian; Cao Peng; He Yonghe; Huang Jiahong; (22 pag.)CN105542751; (2017); B;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 626-40-4,Some common heterocyclic compound, 626-40-4, name is 3,5-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.

Compound II-2 (2.51 g, 10 mmol), Compound III (2.06 g, 10 mmol), Pd(OAc)2 (0.22 g, Lmmol), BINAP (2,2,-bisdiphenylphosphino-1,1′-binaphthyl, 0.62g, 1mmol) and t-BuOK (2.24g, 20mmol) plus Into 50 mL of dry 1,2-dimethoxyethane (DME), the reaction mixture was stirred overnight under a nitrogen atmosphere and TLC detection was performed. The reaction is now complete. The reaction mixture was carefully poured into 200 mL of ice water, stirred, extracted with 50 mL of X 3 CH 2 Cl 2 , and the extraction phases were combined. It was washed with 1% dilute hydrochloric acid and brine and dried over anhydrous sodium sulfate. The desiccant is filtered off with suction and the filtrate is evaporated to dryness on a rotary evaporator. The residue was purified using silica gel column chromatography to give compound IV-2.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3,5-Dibromoaniline, its application will become more common.

Reference:
Patent; Guangdong Sai Bo Technology Co., Ltd.; Guo Huijun; (8 pag.)CN108003169; (2018); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 4549-33-1, 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. 4549-33-1 name is 1,9-Dibromononane, 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.

To a stirred solution of mixture of 3,7-bis(tert-butoxycarbonylamino)-2,8-dimethyl-5- phenylphenazin-5-ium chloride and 3,7-bis(tert-butoxycarbonylamino)-2,6-dimethyl-5- phenylphenazin-5-ium chloride (500 mg, 0.909 mmol) in 10 mL of DMF was added cesium carbonate (738 mg, 2.27 mmol) and stirred at RT for 15 min. The reaction mixture was cooled to 0C and 1,9-dibromononane (156 mg, 0.545 mmol, diluted with 1 mL of DMF) was added dropwise. The reaction mixture was stirred at RT for 12 h. The reaction was monitored by TLC and LCMS. After completion of reaction, the mixture was diluted with ice-cold water and filtered. The solid residue obtained after filtration was dissolved in diethyl ether (200 mL) and washed with brine solution (3×50 mL). The ether layer was dried over anhydrous sodium sulfate, concentrated under reduced pressure to afford the crude product which was purified by column chromatography (neutral alumina, eluent 0-20% EtOAc in hexane) to afford the desired product (mixture of 2 products of same mass) as a dark brown solid (400 mg).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,9-Dibromononane, and friends who are interested can also refer to it.

Reference:
Patent; MEDIVATION TECHNOLOGIES, INC.; RAI, Roopa; PHAM, Son Minh; HART, Barry Patrick; (437 pag.)WO2017/19832; (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. 61613-22-7, name is 2-Bromo-N-phenylaniline, A new synthetic method of this compound is introduced below., HPLC of Formula: C12H10BrN

To obtain the D1-DPS, compound 1a of the -OH formationreaction, and compound 2 of the cyclization reactionwere synthesized. Compound 1 (3 g, 12 mmol) was dissolvedin 50 ml of anhydrous tetrahydrofuran (THF) underhigh purity argon in a one neck round bottom flask. It wascooled to -78 C using solid carbon with acetone and then n-butyllithuim (2.5 M in cyclohexane, 24.7 mmol)was added dropwise slowly. Stirring was continued for 1 h before, cooling for 20-30 min. Then a solution of9-fluorenone (2.4 g, 13.3 mmol) in THF was added at-78 C under an argon atmosphere. The mixture wasstirred for 3 h in the same environment. The reaction was completed after the confirmation of compound 1a. Two side products and reactants appeared by TLC with a solutionof hexane and ethyl acetate (10:1). Additional quenching was not required. The mixture was then worked up using water and dichloromethane. The extracted organiclayer was dried by anhydrous MgSO4. For compound 2, compound 1a was placed in a oneneckround bottom flask, to which, chloroform (10 ml)and methane sulfonic acid (MSA, 5 ml) were added whilestirring at room temperature for 15 min. The progress ofthe reaction was monitored by TLC with a solution of hexane and ethyl acetate (5:1). The resulting mixture wasquenched by saturated aqueous NaHCO3 and extractedwith dichloromethane after the reaction completed. Th esolid product was recrystallized using chloroform and hexane.A slightly yellow solid product was obtained, whichwas then purified by column chromatography with hexane and ethyl acetate.Two intermediates, the DPS acceptor and the compound 2 donor, were reacted for D1-DPS by theBuchwald-Hartwig amination. Compound 2 (0.5 g,1.38 mmol), DPS (0.48 g, 1.38 mmol), pd(dba)2 (0.008 g,0.014 mmol), t-BuONa (0.27 g, 2.77 mmol), and triphenylphosphine(0.003 g, 0.011 mmol) showed high purityAr charging. Then toluene (20 ml) was added and refluxedfor 5 h at 115 C. Quenching was not required. The resultingmixture was worked up using ethyl acetate and water.A small amount of water in the extracted organic layerwas removed by MgSO4 and filtered with celite to removethe inorganic materials. Finally, column chromatographywas applied with hexane and dichloromethane.The white solid product was recrystallized byhexane.

The synthetic route of 61613-22-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Lee, In Hye; Kim, Ki Ju; Kim, Young Kwan; Kim, Young Sik; Shin, Dong Myung; Journal of Nanoscience and Nanotechnology; vol. 19; 8; (2019); p. 4583 – 4589;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 608-30-0, A common heterocyclic compound, 608-30-0, name is 2,6-Dibromoaniline, molecular formula is C6H5Br2N, 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.

(1) Adding 1 mole of 2,6-dibromoaniline to a four-necked flask,Adding 50% sulfuric acid to the flask, stirring was started, and a 15% aqueous solution of sodium nitrite was added dropwise at a temperature of 0-5 C, and the dropping time was 2 hours.After the dropwise addition is kept for 1 hour, 2,6-dibromoaniline is subjected to diazotization reaction at 0 to 5 C under acidic conditions, and the reaction is completed to obtain a dibromoaniline diazonium salt aqueous solution;The molar ratio of 2,6-dibromoaniline to sodium nitrite is 1:1.05, and the molar ratio of sodium nitrite to sulfuric acid is 1:4;(2) adding hypophosphorous acid to the flask in the dibromoaniline diazonium salt aqueous solution prepared in the step (1), then raising the temperature to 70-80 C, and maintaining the reaction for 3 hours to obtain a mixed solution containing m-dibromobenzene. ; the molar ratio of hypophosphorous acid to 2,6-dibromoaniline is 1.3:1;(3) The mixture obtained in the step (2) is allowed to stand for 30 minutes to be layered, and then the inorganic phase and the organic phase are separated, the organic phase is washed with water, and the inorganic phase and the organic phase are separated by standing. The organic phase can be distilled under reduced pressure to obtain m-dibromobenzene; the calculated yield is over 81%, and the detection purity is over 98%.

The synthetic route of 608-30-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shandong Tianyi Chemical Co., Ltd.; Tang Xingsan; Xing Xiaohua; Zhang Ming; (6 pag.)CN110078587; (2019); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 22385-77-9,Some common heterocyclic compound, 22385-77-9, name is 1-Bromo-3,5-di-tert-butylbenzene, molecular formula is C14H21Br, 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.

The reaction flask was sequentially charged with raw materials la (56 mg, 0.2 mmol) and 21 (1 mL), cesium carbonate (130 mg, 2.0 eq), dilute ligand L2-1 (2.6 mg, 5 molpercent), tricyclohexylphosphine tetrafluoroboron Acid salt (1.8 mg, 2.5 molpercent), [Rh (cod) Cl] 2 (2.5 mg, 2.5 molpercent), di-tert-butylphosphonium chloride (18 mg, 0.1 mmol) and toluene (2 mL) in nitrogen In an atmosphere, the mixture was stirred at 120 ° C for 24 hours, cooled to room temperature, diluted with ethyl acetate (5 mL), diluted with EtOAc (2 mL), and brine (5 mL) After spin-drying column chromatography, the eluent was (ethyl acetate/petroleum ether = 1/15) to give product 3a as a white solid 24 mg, yield 18percent.

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-3,5-di-tert-butylbenzene, its application will become more common.

Reference:
Patent; UNIV NANKAI; Nankai University; YE MENGCHUN; Ye Mengchun; YANG JINFEI; Yang Jinfei; (18 pag.)CN107840784; (2018); A;,
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. 54962-75-3, name is 3-Bromo-5-(trifluoromethyl)aniline, A new synthetic method of this compound is introduced below., COA of Formula: C7H5BrF3N

INTERMEDIATE 13 -( 1 H- 1 ,2,4-Triazol- 1 -yl)-5-(trifluoromethyl)aniline[00146] 3-Bromo-5-(trifluoromethyl)aniline (3.5 g, 14.6 mmol), copper(I) iodide (1.39g, 7.3 mmol), potassium carbonate (6.0 g, 43.7 mmol) and lH-l,2,4-triazole (3.0 g, 43.7 mmol) in NMP (10 mL) were heated at 195 0C for 2 hours. The reaction mixture was filtered through a plug of silica gel, washed with ethyl acetate, and concentrated. The crude residue was purified by silica gel column chromatography (stepwise gradient, from hexanes to 75% ethyl acetate/hexanes). The fractions were concentrated, dissolved in diethyl ether (150 mL), washed with water (4 x 50 mL), dried over Na2SO4, filtered and concentrated to afford Intermediate 1 (1.95 g, 58.6 % yield) as a tan solid. HPLC: Rt = 1.193 min. (PHENOMENEX Luna 5 micron C18 4.6 x 30 mm, 10-90% aqueous methanol containing 0.1% TFA, 2 min. gradient, flow rate = 5 mL/min., detection at 254 nm). MS (ES): m/z = 229.01 [M+H]+. 1H NMR (500 MHz, DMSOd6) delta ppm 8.27 (1 H, s), 7.34 (1 H, s), 6.47 (2 H, d, J = 2.29), 6.14 (1 H, s). Intermediate 1 was used in the synthesis of Examples 13, 104, 165, 169, and175.

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; BRISTOL-MYERS SQUIBB COMPANY; FINK, Brian; CHEN, Libing; GAVAI, Ashvinikumar; HE, Liqi; KIM, Soong-Hoon; NATION, Andrew; ZHAO, Yufen; ZHANG, Litai; WO2010/42699; (2010); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 1435-53-6,Some common heterocyclic compound, 1435-53-6, name is 2,4-Dibromo-1-fluorobenzene, molecular formula is C6H3Br2F, 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.

General procedure: 8.10 1-(2′,5′-Dimethoxyphenyl)-3-(2′,5′-dimethoxyphenyl)-4-fluorobenzene (11j): Starting with 10 (100 mg, 0.39 mmol), Cs2CO3 (253 mg, 0.78 mmol), Pd(PPh3)4 (3 mol%), 2,5-dimethoxyphenylboronic acid (158 mg, 0.85 mmol) and 1,4-dioxane (4 mL), 11j was isolated as a colorless solid (91 mg, 65%). Mp 149-150 C. 1H NMR (300 MHz, CDCl3): delta = 3.68 (s, 3H, CH3), 3.69 (s, 3H, OCH3), 3.71 (s, 6H, OCH3), 6.70-6.80 (m, 6H, ArH), 7.04-7.10 (m, 1H, ArH), 7.40-7.45 (m, 2H, ArH). 13C NMR (75 MHz, CDCl3): delta = 55.8 (2OCH3), 56.3 (OCH3), 56.4 (OCH3), 112.4 (CH), 112.6 (CH), 113.2 (CH), 114.2 (CH), 115.1 (d, J = 22.6 Hz, CH), 116.7 (CH), 117.1 (CH), 125.6 (d, J = 16.4 Hz, C), 126.0 (C), 130.3 (d, J = 7.6 Hz, CH), 130.5 (C), 132.8 (d, J = 4.0 Hz, CH), 134.0 (d, J = 3.5 Hz, C), 150.7 (C), 151.3 (C), 153.5 (C), 153.8 (C), 159.3 (d, JCF = 249.0 Hz, CF). 19F NMR (282 MHz, CDCl3): delta = -116.3 (CF). IR (ATR, cm-1): , 3021 (w), 2948 (w), 2832 (w), 1582 (w), 1486 (s), 1463 (m), 1407 (m), 1381 (m), 1295 (m), 1264 (m), 1220 (s), 1174 (s), 1113 (m), 1049 (s), 1023 (s), 915 (w), 855 (m), 803 (m), 755 (w), 706 (s), 5651 (w), 568 (w), 507 (w), 468 (w) cm-1. MS (EI, 70 eV): m/z (%) = 368 (100) [M]+, 339 (12), 338 (57), 169 (12). HRMS (ESI) calcd. for C22H22O4F [M + H]+: 369.14966; found 369.14871.

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

Reference:
Article; Sharif, Muhammad; Maalik, Aneela; Reimann, Sebastian; Feist, Holger; Iqbal, Jamshed; Patonay, Tamas; Villinger, Alexander; Langer, Peter; Journal of Fluorine Chemistry; vol. 146; (2013); p. 19 – 36;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 185122-74-1, 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. 185122-74-1 name is 5-Bromo-2,3-dihydro-1H-inden-1-amine, 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 C (2.5 g, 10.5 MMOL) was dissolved in MEOH (40 mL) and reacted with SNCI2-2H2O (4. 7 g, 20.8 MMOL) at rt overnight. The solvent was removed and NAOH (aq, 1 N, 50 mL) was added. The reaction mixture was extracted into EtOAc (50 mL). The organic layer was extracted with HCI (1 N, 50 mL x 2) and the aquoues layer was basified with solid NaOH until the pH was about 11. The mixture was extracted with EtOAc (50 mL x 3). The organic layers were combined and dried over NA2SO4 and then concentrated to give the corresponding amine. The amine was dissolved in CH2CI2 (50 mL) and cooled TO-78 C. TFAA (1.47 g, 6.9 MMOL) was added followed by slow addition of Et3N (1.05 g, 10.4 MMOL). The reaction mixture was slowly warmed up to rt and stirred for 3 h. H20 (50 mL) was used to wash the reaction mixture. The organic layer was washed with brine, then dried over NA2SO4, and concentrated to dryness. The crude product was purified via sgc (25% EtOAc/hexanes) to give 3.1 g (96%) of compound D.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Bromo-2,3-dihydro-1H-inden-1-amine, and friends who are interested can also refer to it.

Reference:
Patent; SCHERING CORPORATION; WO2004/48322; (2004); A1;,
Bromide – Wikipedia,
bromide – Wiktionary