Month: June 2021

Reference of 583-68-6, 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. 583-68-6 name is 2-Bromo-4-methylaniline, 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.

General procedure: To a solution of 2-bromoaniline (5 g, 29 mmol) dissolved in CH3CN (80 mL) was added aq. HCl (15 mL conc. HCl in 50 mL water), then the mixture was cooled to 0 C, and it was added a solution of NaNO2 (2.4 g, 34.87 mmol) in water (50 mL). After addition, the reaction was kept at the temperature lower than 5 C for 30 min and it was added a solution of (7.23 g, 43.59 mmol) in water (50 mL). After addition, the reaction was kept at room temperature overnight, poured into water (300 mL) and extracted with CH2Cl2.The organic phase was dried over MgSO4. After workup, the brown oily product was distilled to afford a pale-yellow.

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

Reference:
Article; Lv, Jun; Liu, Qiancai; Tang, Jie; Perdih, Franc; Kranjc, Kristof; Tetrahedron Letters; vol. 53; 39; (2012); p. 5248 – 5252;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 13194-73-5,Some common heterocyclic compound, 13194-73-5, name is 3,5-Dibromo-4-methylaniline, molecular formula is C7H7Br2N, 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 round-bottom flask were added sulfoacetic acid (0.14g, 1.0 mmol), DMF (5 mL), HBTU (0.379g, 1 mmol), 3,5-dibromo-4- methylaniline (0.265g, 1 mmol), DIEA (0.52 mL, 3 mmol), and DMAP (0.012g, 0.1 mmol). The mixture was stirred at room temperature for 2 hours, and then it was subjected to reversed- phase HPLC purification to give product L335-M34 as a white solid (0.385g, 99% yield): 1H NMR (500 MHz, DMSO) delta 10.08 (s, 1H), 7.87 (s, 2H), 3.52 (s, 2H), 2.42 (s, 3H); 13C NMR (DMSO) delta 164.6, 138.9, 130.5, 124.1, 121.8, 59.1, 22.6; ESI-HRMS calcd for (M + H+) 385.8692, found 385.8696

The synthetic route of 13194-73-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; INDIANA UNIVERSITY RESEARCH & TECHNOLOGY CORPORATION; ZHANG, Zhong-Yin; HE, Rongjun; (128 pag.)WO2016/196591; (2016); 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. 33070-32-5, name is 5-Bromo-2,2-difluorobenzodioxole, A new synthetic method of this compound is introduced below., name: 5-Bromo-2,2-difluorobenzodioxole

Step 1: (S)-Methyl2-(tert-butoxycarbonyl)-3-(2,2-difluorobenzo[d][1,3]dioxol-5-yl) propanoate To a 25 mL RBF was added zinc powder (1.03 g, 15.8 mmol) and iodine (0.0161 g, 0.0633 mmol). The mixture was heated with a heat gun for 5 minutes and the resulting mixture was then flushed with nitrogen 3 times and allowed to cool to rt. A solution of (R)-methyl2-(tert-butoxycarbonyl)-3-iodopropanoate (3.47 g, 10.5 mmol) in 5 mL of DMF was added dropwise to the mixture over 3 minutes and the resulting grey slurry was stirred at 0 C. for 20 minutes before being warmed to rt. After stirring at rt for 30 minutes, 5-bromo-2,2-difluorobenzo[d][1,3]dioxole (2.50 g, 10.5 mmol), Pd2(dba)3 (0.193 g, 0.211 mmol) and S(Phos) (0.346 g, 0.844 mmol) were added and the reaction mixture was heated to 40 C. for 2 hours. The resulting mixture was cooled to rt and partitioned between ethyl acetate (50 mL) and a solution of ~9:1 saturated ammonium chloride/ammonium hydroxide pH=9 (250 mL). The aqueous layer was extracted with ethyl acetate (3*100 mL) and the combined organic layers were washed with water, brine, and dried over sodium sulfate. Concentration of the filtered solvents and purification of resulting crude material by silica gel chromatography provided (S)-methyl 2-(tert-butoxycarbonyl)-3-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)propanoate (1.89 g, 49.9% yield) as a slightly brown oil.

The synthetic route of 33070-32-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Amgen Inc.; US2010/120774; (2010); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 142808-15-9, 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. 142808-15-9 name is 4-Bromo-2-fluorobenzotrifluoride, 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.

Into a 50 mL dry, round bottom flask fitted with a magnetic stirring bar, a dropping funnel (25 mL) and a refluxing condenser was placed magnesium turnings (129 mg, 5.3 mmol) and anhydrous diethyl ether (4 mL). Anhydrous diethyl ether (16 mL) was added to the dropping funnel followed by 4-bromo- 2-fluoro-1-(trifluoromethyl)benzene (1.17 g, 4.8 mmol). A portion of the 4- bromo-2-fluoro-1-(trifluoromethyl)benzene solution (2 mL) as well as iodine (5 mg) was added to the flask which was then heated to reflux and stirred. Heating was stopped and the remainder of the 4-bromo-2-fluoro-1- (trifluoromethyl)benzene solution was added dropwise to the flask at such a rate that the solvent refluxed gently (about 10 minutes). After the addition was complete, the reaction was heated to reflux for 2 hours. The mixture was cooled to -78 C and a solution of 2-(2,6,6-trimethylcyclohex-1- enyl)acetaldehyde (200 mg, 1.2 mmol) in diethyl ether (3 mL) was added dropwise via syringe. The reaction was allowed to warm to room temperature and stirred for 4 hours. The reaction was quenched by addition of saturated aqueous ammonium chloride (10 mL). The mixture was diluted with water (20 mL) and the organics were extracted with diethyl ether (30 mL x 2). The combined organic phase was washed with brine (60 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: petroleumether/ethyl acetate = 100/1 ) to afford the title compound as a yellow oil (138 mg, Yield: 35%). Rf = 0.6 (10:1 petroleum ether/ethyl acetate); 1H NMR (400 MHz, CDCI3) delta 7.57 (t, J = 7.6 Hz, 1 H), 7.30-7.23 (m, 2H), 4.89 (t, J = 7.4 Hz, 1 H), 2.48-2.46 (m, 2H), 2.22 (d, J = 1 .2 Hz, 1 H), 2.12-1.96 (m, 2H), 1.68 (s, 3H), 1 .68-1 .62 (m, 2H), 1 .51 -1 .48 (m, 2H), 1 .07 (s, 3H), 1.06 (s, 3H) ppm; Mass spectrum (ESI +ve) m/z 331 (M + H+).

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

Reference:
Patent; BIKAM PHARMACEUTICALS, INC.; QUACH, Tan; BERMAN, Judd; GARVEY, David, S.; WO2013/81642; (2013); 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. 58534-95-5, name is 3-Bromo-2-fluoroaniline, This compound has unique chemical properties. The synthetic route is as follows., Safety of 3-Bromo-2-fluoroaniline

A mixture of 2,2,2-Trichloroethane-1,1-diol (8.09 g, 49.33 mmol) and Na2SO4 (53 g, 370 mol) were dissolved in water and warmed to 35C. 3-bromo-2- fluorobenzenamine (7.77 g, 41.11 mmol) in water was added, followed by 35% aqueous HC1 (4.6 mL) and hydroxylamine hydrochloride (9.08 g, 131.6 mol). The resultingmixture was heated to 90C for 16 h and yellow precipitate was formed. The mixture was cooled to room temperature, the solid was filtered, washed with water, and dried in the air to afford the desired product (6.5 g, 61% yield)

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 58534-95-5.

Reference:
Patent; ARAXES PHARMA LLC; LI, Liansheng; FENG, Jun; LONG, Yun Oliver; LIU, Yuan; WU, Tao; REN, Pingda; LIU, Yi; (246 pag.)WO2017/87528; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 10269-01-9, These common heterocyclic compound, 10269-01-9, name is (3-Bromophenyl)methanamine, 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.

(2S)-1 -[(tert-butoxy)carbonyl]pyrrolidine-2-carboxylic acid (6.45 g, 29.97 mmol, 1 .00 equiv), HOBT (4.05 g, 29.97 mmol, 1 .00 equiv), EDCI (5.76 g, 30.05 mmol, 1 .00 equiv), and (3- bromophenyl)methanamine (5.55 g, 29.83 mmol, 1 .00 equiv) were dissolved in Nu,Nu-dimethylformamide at room temperature. The reaction was stirred for 2 h. Then it was quenched by the addition of water. The resulting solution was extracted with ethyl acetate and the organic layers were combined and washed with 3×50 mL of saturated aqueous sodium bicarbonate, brine, and concentrated in vacuo. This resulted in 1 0 g (87%) of tert-butyl (2S)-2-[[(3-bromophenyl)methyl]carbamoyl]pyrrolidine-1 -carboxylate as a white solid.

The synthetic route of 10269-01-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ZALICUS PHARMACEUTICALS, LTD.; SHORT, Glenn, F., III; ROMERO, Donna, L.; LEE, Margaret, S.; WO2015/130957; (2015); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 33070-32-5, These common heterocyclic compound, 33070-32-5, name is 5-Bromo-2,2-difluorobenzodioxole, 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.

EXAMPLE 89E 2.2-difluoro-1,3-benzodioxol-5-ylboronic acid A solution of 5-bromo-2,2-difluorobenzodioxole (1.18 g, 4.97 mmol) in anhydrous diethyl ether (8 mL) at -78 C. was treated with 2.5M n-BuLi in hexane (2.4 mL, 5.97 mmol), stirred for 1 hour, and treated with triisopropyl borate (1.5 mL, 6.46 mmol). The mixture was slowly warmed to room temperature and stirred for about 18 hours. The reaction was quenched with saturated NH4Cl/10% HCl and extracted with ethyl acetate. The combined extracts were dried (MgSO4), filtered, and concentrated. The concentrate was used directly without further purification. 1H NMR (CD3OD) delta 7.26-7.11 (m, 3H).

Statistics shows that 5-Bromo-2,2-difluorobenzodioxole is playing an increasingly important role. we look forward to future research findings about 33070-32-5.

Reference:
Patent; Claiborne, Akiyo K.; Gwaltney, II, Stephen L.; Hasvold, Lisa A.; Li, Qun; Li, Tongmei; Lin, Nan-Horng; Mantei, Robert A.; Rockway, Todd W.; Sham, Hing L.; Sullivan, Gerard M.; Tong, Yunsong; Wang, Gary; Wang, Le; Wang, Xilu; Wang, Wei-Bo; US2002/115640; (2002); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 17247-58-4, These common heterocyclic compound, 17247-58-4, name is (Bromomethyl)cyclobutane, 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 12.3 g (83 mmol) of cyclobutylcarbinyl bromide (Aldrich) and 13.7g (91 mmol) of sodium iodide in 150 mL of acetone wasrefluxed overnite and then cooled to rt. The inorganic solids were filtered off and the acetone and cyclopropylcarbinyl iodide (8.41g, 46%) distilled off at ambient and 150 torr at 80 C, respectively. A solution of 4.0 g (21.98 mmol) of cyclobutyl carbinyl iodide in 30mL of anhydrous diethyl ether(Et20) cooled to-78 C was cannulated into a solution of 17 mL (21.98 mmol) of 1.3M sec-butyl lithium in cyclohexanes and the solution was stirred for 5 min. To this mixture was cannulated a solution of 3.0 g (21.98 mmol) of freshly distilled sulfuryl chloride in 110mL of hexanes cooled to-78 C, the mixture warmed to rt over 1 h and was then carefully concentrated in vacuo. This mixture was redissolved inEt20, washed once with some ice-cold water, dried(MgS04) and concentrated carefully. This mixture was redissolved in 30mL of THF, added dropwise to 500 mL of saturated NH3 in THF and was allowed to stirovernite. The mixture was concentrated in vacuo to a crude yellow solid and was recrystallized from the minimum amount ofCH2Cl2 in hexanes with 1-2 drops of MeOH to afford 1.39 g(42%) of cyclobutyl carbinylsulfonamide as a whitesolid.’H NMR(CDCI3) 1.81-2. 03 (m, 4H), 2.14-2. 28 (m, 2H), 2.81-2. 92 (m,1H), 3.22 (d, J=7 Hz, 2H), 4.74 (brs, 2H); 3C NMR (CD3)8 19.10, 28.21, 30.64, 60.93 ; MS m/e 148(M-l)-. time: 1.73, method B), 818 (M++H).

Statistics shows that (Bromomethyl)cyclobutane is playing an increasingly important role. we look forward to future research findings about 17247-58-4.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2003/99274; (2003); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 626-88-0, 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 626-88-0 as follows.

General procedure: To a solution of compound 3 (0.46 g, 2 mmol), in dry DMF (5 mL), and anhydrous potassium carbonate (0.5 g, 3.4 mmol) and,an appropriate bromoalkyl halide (2 equivalent) was added. Themixturewas heated for 12 h at 80 C, and then the reaction mixturewas poured over crushed ice, filtered and washed with water toyield the desired product. The isolated crude materials were furtherpurified by silica gel chromatography, using EtOAc-hexane (3:7) toprovide the desired products. The physical characteristics andspectral data of separated products are listed below.

According to the analysis of related databases, 626-88-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Yahia, Eman; Mohammad, Haroon; Abdelghany, Tamer M.; Fayed, Eman; Seleem, Mohamed N.; Mayhoub, Abdelrahman S.; European Journal of Medicinal Chemistry; vol. 126; (2017); p. 604 – 613;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 51436-99-8, These common heterocyclic compound, 51436-99-8, name is 4-Bromo-2-fluorotoluene, 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.

Example 29 Preparation of 2-fluoro-4-cyanotoluene (38) Copper(I) cyanide (Aldrich, 3.6 g, 40 mmol) was added to a solution of 4-bromo-2-fluorotoluene (Aldrich, 5 g, 27 mmol) in DMF (60 mL). The reaction mixture was heated at 150 C. for 11 hours. After cooling to room temperature, the mixture was partitioned between water and EtOAc (500 mL each). The organic layer was dried (MgSO4), and solvent was removed under vacuum to give the title compound (2.08, 58%). 1H-NMR (CDCl3) delta2.36 (s, 3H), 7.30 (m, 3H), 7.35 (d, 1H, J=8.1 Hz).

The synthetic route of 51436-99-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Corvas International, Inc.; US6541467; (2003); B1;,
Bromide – Wikipedia,
bromide – Wiktionary