Month: March 2021

Application of 4333-56-6,Some common heterocyclic compound, 4333-56-6, name is Bromocyclopropane, molecular formula is C3H5Br, 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.

INTERMEDIATE 36; 1-bromo-3-cyclopropoxybenzene A mixture of 3-bromophenol (2.4g, 13.9mmol), bomocyclopropane (6.66ml, 83mmol) and potassium carbonate (9.6g, 69.5mmol) in DMF (16ml) was heated at 18O0C in a microwave oven for 8 hours. The reaction mixture was diluted with a mixture of diethylether and water. The organic layer was separated, washed with water, brine, dried over Na2SO4, filtered and evaporated. An oil was obtained, 2.87g, with a purity of 81%. This intermediate was used for the next reaction. Retention time: 6.91 min.

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

Reference:
Patent; LABORATORIOS ALMIRALL, S.A.; WO2008/77639; (2008); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

6274-57-3, name is 1-(4-Bromophenyl)-N,N-dimethylmethanamine, 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: 6274-57-3

General procedure: At room temperature, organic carbonyl acid 3 (R-COOH, 0.5 mmol) was added into a reaction tube equipped with a small magnet. Then a solution of tertiary amine 1 (R1CH2-NR2R3, 0.5 mmol ) in DCM (2.5 mL) was added dropwise in 2 min. After the mixture was stirred at room temperature for a few minutes, 1 equivalents of dimethyl acetylenedicarboxylate (DMAD, 2) was added. The reaction was stirred overnight at room temperature, and then monitored by TLC with silica gel coated plates. After being stirred for 14 h, the solvent was removed and the residue was purified by a flash column chromatography with silica gel with ethyl acetate/hexane (1:25-30) as eluent to give the desired products 4, 5, and 7. Most of compounds are known and confirmed by NMR, ESI-MS, IR.

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

Reference:
Article; Shen, Hao; Lu, Xing; Jiang, Ke-Zhi; Yang, Ke-Fang; Lu, Yixin; Zheng, Zhan-Jiang; Lai, Guo-Qiao; Xu, Li-Wen; Tetrahedron; vol. 68; 43; (2012); p. 8916 – 8923;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 55289-36-6, name is 3-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 55289-36-6, SDS of cas: 55289-36-6

A suspension of 8-fluoro-lH-benzo[d][l,3]oxazine-2,4-dione (3.00 g, 16.6 mmol) in xylenes (50 mL) was treated with 3-bromo-2-methylaniline (3.08 g, 16.6 mmol) and heated to reflux. After 6 hours, the mixture was allowed to cool to room temperature overnight. The resulting suspension was diluted with hexanes and the precipitate was collected by filtration, rinsed with hexanes and air-dried to provide 2-amino-N-(3-bromo- 2-methylphenyl)-3-fluorobenzamide as a white solid (4.50 g, 84% yield). Mass spectrum m/z 323, 325 (M+H)+. 1H NMR (400 MHz, chloroform-d) delta 7.69 (d, J=7.9 Hz, 1H), 7.65 (br. s., 1H), 7.50-7.46 (m, 1H), 7.32 (d, J=8.1 Hz, 1H), 7.19-7.1 1 (m, 2H), 6.73-6.64 (m, 1H), 5.69 (br. s., 2H), 2.44 (s, 3H).

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

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; KO, Soo Sung; BATT, Douglas A.; BERTRAND, Myra Beaudoin; DELUCCA, George V.; LANGEVINE, Charles M.; LIU, Qingjie; SRIVASTAVA, Anurag S.; WATTERSON, Scott Hunter; WO2014/210087; (2014); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 50548-45-3, These common heterocyclic compound, 50548-45-3, name is 1-Bromodibenzo[b,d]furan, 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.

30.0 g (177 mmol, 1.0 eq) of 4-aminobiphenyl are initially charged together with 43.7 g (177 mmol, 1.0 eq) of 1-bromodibenzofuran and 23.4 g (212 mmol, 1.20 eq) of sodium tert-pentoxide [14593-46-5] in 600 ml of absolute toluene and degassed for 30 minutes. Subsequently, 398 mg (1.77 mmol, 0.01 eq) of palladium(II) acetate [3375-31-3] and 1.46 g (3.56 mmol, 0.02 eq) of 2-dicyclohexylphos- phino-2?,6?-dimethoxybiphenyl SPHOS [657408-07-6] are added and the mixture is heated under reflux overnight. After the reaction has ended, the mixture is cooled down to room temperature and extracted with 500 ml of water. Subsequently, the aqueous phase is washed three times with toluene, the combined organic phases are dried over sodium sulphate and the solvent is removed on a rotary evaporator. The brown residue is taken up in about 200 ml of toluene and filtered through silica gel. For further purification, a recrystallization from toluene/heptane is conducted. Yield: 44 g (133 mmol), 76percent of theory.

Statistics shows that 1-Bromodibenzo[b,d]furan is playing an increasingly important role. we look forward to future research findings about 50548-45-3.

Reference:
Patent; Merck Patent GmbH; PARHAM, Amir Hossain; EBERLE, Thomas; JATSCH, Anja; GROSSMANN, Tobias; KROEBER, Jonas Valentin; MONTENEGRO, Elvira; JOOSTEN, Dominik; WERN, Caroline; (238 pag.)US2019/119260; (2019); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 33070-32-5, A common heterocyclic compound, 33070-32-5, name is 5-Bromo-2,2-difluorobenzodioxole, molecular formula is C7H3BrF2O2, 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) 2,2-Difluoro-5-(3-fluoro-4-nitrophenyl)-1 ,3-benzodioxoleA slurry of 5-bromo-2,2-difluoro-1 ,3-benzodioxole (1.23 g, 5.2 mmol), 4-N- BOC-amino-3-fluorophenylboronic acid (1.58 g, 6.2 mmol), [1,1′- bis(diphenylphosphino)ferrocene]dichloropalladium (II) dichloromethane adduct (0.131 g, 0.16mmol), and 2M aqueous sodium carbonate solution (7.8 mL, 15.6 mmol) in 1 ,4-dioxane (25.0 mL) was heated at reflux for 2.5 hours then cooled to ambient temperature. The reaction was dried over sodium sulfate then filtered and evaporated under reduced pressure to a residue. Purification by column chromatography on silica (0-65% gradient of ethyl acetate in hexanes) gave 1 ,1- dimethylethyl [4-(2,2-difluoro-1 ,3-benzodioxol-5-yl)-2-fluorophenyl]carbamate as a waxy white solid (54%).A solution of 1 ,1-dimethylethyl [4-(2,2-difluoro-1 ,3-benzodioxol-5-yl)-2- fluorophenyl]carbamate (0.992 g, 2.70 mmol) in 1 :1 trifluoroacetic acid and dichloromethane (20 mL) was stirred at ambient temperature for 1.5 hours then EPO evaporated under reduced pressure. The resulting residue was treated with glacial acetic acid (20.0 ml_) and sodium perborate tetrahydrate (2.08 g, 13.5 mmol) then heated at 75 2C for 3 hours. The reaction was cooled to ambient temperature then poured onto ice (120 g). After 1 hour, the slurry was filtered and the collected solids were rinsed with water then suction dried. Purification of the solids by silica chromatography (0 to 50% gradient of ethyl acetate in hexanes) gave the title compound (0.249 g, 31%) as a yellow solid. MS (ES) m/e 298 (M + H)+.

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

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2006/113432; (2006); A2;,
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. 460-00-4, name is 1-Bromo-4-fluorobenzene, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C6H4BrF

General procedure: A solution of precatalyst 2 (9.0 mg, 0.01 mmol, 1.0 mol%) in dry THF (1.5 mL) was stirred for 5 min at ambient temperature under N2. Then, bromobenzene (157 mg, 1.0 mmol) was added via syringe and the solution stirred for 5 min. Thereafter, 4-methoxyphenyl boronic acid (167 mg, 1.1 mmol) was added along with Na2CO3 (1 M (aqueous), 1 mL), and the resulting solution was stirred at 60 C for 3 h. At ambient temperature, aqueous H2O (10 mL) was added and the organic layer was extracted with EtOAc (3 x 10 mL). The combined organic layers were concentrated in vacuo and the remaining residue was purified by column chromatography (n-hexane/EtOAc: 200/1) to yield 4-Methoxybiphenyl (160 mg, 87%) as a colorless solid

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 460-00-4.

Reference:
Article; Shah, Parin; Santana, M. Dolores; Garcia, Joaquin; Serrano, J. Luis; Naik, Minal; Pednekar, Suhas; Kapdi, Anant R.; Tetrahedron; vol. 69; 5; (2013); p. 1446 – 1453;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 7745-91-7, 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. 7745-91-7, name is 3-Bromo-4-methylaniline, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a well stirred solution of compound 6a or 6b (0.2 g, 1 Eq.) in absolute ethanol (10 mL), the appropriately substituted anilines(1.1 Eq) was added and the reaction mixture was refluxed for 2-3 h until TLC showed full consumption of starting materials. The excess of solvent was evaporated under reduced pressure to yield the crude solids, which were further purified by recrystallization with methanol to afford the desired title compounds (7-43).

The chemical industry reduces the impact on the environment during synthesis 3-Bromo-4-methylaniline. I believe this compound will play a more active role in future production and life.

Reference:
Article; Cherukupalli, Srinivasulu; Chandrasekaran, Balakumar; Kry?tof, Vladimir; Aleti, Rajeshwar Reddy; Sayyad, Nisar; Merugu, Srinivas Reddy; Kushwaha, Narva Deshwar; Karpoormath, Rajshekhar; Bioorganic Chemistry; vol. 79; (2018); p. 46 – 59;,
Bromide – Wikipedia,
bromide – Wiktionary

129316-09-2, name is 1,3-Dibromo-5-(tert-butyl)benzene, 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. Product Details of 129316-09-2

(4) (Suzuki) by Suzuki coupling reaction to obtain the final product f: the 9 – benzene anthracene -10 borate 10 mmol, 1, 3 – dibromo – 4, 6 – dihydro -5 – tert butyl 2 mmol, four (triphenylphosphine) palladium 0.4 mmol, toluene 80 ml, ethanol 20 ml, K2CO344 MmoL (for 20 ml distilled water into the solution), is added to the reaction bottle, then the system vacuum, in 110 C under the protection of nitrogen reflux 24 hours. After the completion of the reaction, methanol hot washing and filtering, toluene recrystallization, distillation to obtain the final product f. Yield 66%.

The synthetic route of 129316-09-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shaanxi Normal University; Hu Jianyong; Zhang Jiali; Zhao Zhen; Duan Xuewei; (18 pag.)CN109678645; (2019); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 627871-16-3,Some common heterocyclic compound, 627871-16-3, name is 5-Bromo-4-fluoro-2-methylaniline, molecular formula is C7H7BrFN, 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 solution of vinylidene chloride (127 ml), tert-butyl nitrite (19 ml) and copper(ll)chloride (18.4 g) in acetonitrile (150 ml) is added a solution of 5-bromo-4-fluoro-2-methyl-phenylamine (Bioorganic & Medicinal Chemistry Letters (2006), 16(2), 457-460) (21.5 g) in acetonitrile (100 ml) dropwise below 200C. The reaction mixture is stirred at room temperature for 48 hours, poured on diluted HCI and extracted with fert-butyl methyl ether (3x). The combined organic layers are washed with brine, dried over sodium sulfate and concentrated. The residue is purified by chromatography on silica gel (ethyl acetate/cyclohexane 1 :4). Yield: 29.20 g of 1-bromo-2-fluoro- 4-methyl-5-(2,2,2-trichloro-ethyl)-benzene as an oil.1H-NMR (CDCI3): 2.42 (s, 3H), 3.93 (s, 2H), 7.00 (d, 3J(H,F)=9.2Hz, 1 H), 7.69 (d, 4J(H,F)=7.0Hz, 1 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromo-4-fluoro-2-methylaniline, its application will become more common.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; ZAMBACH, Werner; HUETER, Ottmar Franz; WENGER, Jean; GOEGHOVA, Marcela; PITTERNA, Thomas; MAIENFISCH, Peter; JEANMART, Stephane Andre Marie; MUEHLEBACH, Michel; WO2010/52161; (2010); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 15155-41-6, 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 15155-41-6 as follows.

Synthesis of 3,6-dibromobenzene-1,2-diamine: Dibromobenzo[c][1,2,5]thiadiazole (2.29 g, 10 mmol) and sodiumborohydride (5.7 g, 150 mmol) were added to ethanol at 0 Cand stirred at room temperature for 36 h. The solution wasadded water and ethyl acetate then was separated by separatoryfunnel. The organic layer was dried over MgSO4 then concentrated under reduced pressure and purified by chromatographyon a silica column eluting with petroleum ether/ethyl acetate(5:1, v/v) to afford a yellow solid (1.9 g, 71 % yield). 1H NMR(400 MHz, CDCl3, ppm) delta-aromatic H, 6.86 (d, 2H), 3.92 (s,4H); 13C NMR (100 MHz, CDCl3, ppm): 133.73,123.27, 109.70.

According to the analysis of related databases, 15155-41-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Sun, Xiaoxia; Lei, Xiaolong; Hu, Yu; Asian Journal of Chemistry; vol. 27; 7; (2015); p. 2427 – 2430;,
Bromide – Wikipedia,
bromide – Wiktionary