Category: bromides-buliding-blocks

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

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

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

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

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

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

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

Reference of 656-64-4, These common heterocyclic compound, 656-64-4, name is 3-Bromo-4-fluoroaniline, 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.

General procedure: (Z)-N-(3-Bromo-4-fluorophenyl )-N’-hydroxy-1H-indazole-7-carboximidamide (8a). To a solution of 7 (25 mg,0.105 mmol) in THF (1 mL) at 60 C was 3-bromo-4-fluoroaniline (20 L, 0.105 mmol) was added andstirred for 10 min. A solution of NaHCO3 (13 mg, 0.157 mmol) in water (1 mL) was added dropwiseand stirred at 60 C for 3 h. The mixture was extracted with EA and washed with brine. The organic layer was dried over MgSO4 and concentrated to obtain the crude mixture which was purified bycolumn chromatography (MPLC) to give compound 8a.

Statistics shows that 3-Bromo-4-fluoroaniline is playing an increasingly important role. we look forward to future research findings about 656-64-4.

Reference:
Article; Lee, Dong-Ho; Lee, Joo-Youn; Jeong, Jieun; Kim, Miok; Lee, Kyung Won; Jang, Eunseo; Ahn, Sunjoo; Lee, Chang Hoon; Hwang, Jong Yeon; Molecules; vol. 22; 11; (2017);,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 630-17-1, 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. 630-17-1, name is 1-Bromo-2,2-dimethylpropane, This compound has unique chemical properties. The synthetic route is as follows.

40 This method was used for the synthesis of neopentylphenyl sulfide, 5h.1-Bromo-2,2-dimethyl propane (3.02 g, 20 mmol), aqueousbenzenethiolate (20 mmol), and Aliquat 336 (0.033 mol equiv)were added to a 2-neck round-bottom flask under nitrogen. Themixture was heated at 70 C with vigorous stirring for 16 h. After themixture had cooled to room temperature, the organic layer wasseparated and the aqueous phase was extracted with two 20 mLportions of diethyl ether. The combined organic phases were washedwith 20 mL of 10% aqueous sodium chloride and dried overmagnesium sulfate. After removal of the solvent, the resulting residualoil was distilled using a Kugelrohr apparatus to give neopentyl phenylsulfide, bp 145-147 (0.1 mm. Hg).

The chemical industry reduces the impact on the environment during synthesis 1-Bromo-2,2-dimethylpropane. I believe this compound will play a more active role in future production and life.

Reference:
Article; O’Mahony, Graham E.; Eccles, Kevin S.; Morrison, Robin E.; Ford, Alan; Lawrence, Simon E.; Maguire, Anita R.; Tetrahedron; vol. 69; 47; (2013); p. 10168 – 10184;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 314084-61-2, These common heterocyclic compound, 314084-61-2, name is 2-Bromo-1,3-diethyl-5-methylbenzene, 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) Under a nitrogen atmosphere and at normal pressure, 7 g of malonic acid dinitrile dissolved in 3.5 ml of 1-methyl-2-pyrrolidone are added dropwise in the course of 30 minutes, at from 20 to 30C, to a mechanically stirred mixture of 12 g of sodium hydroxide (pellets) in 150 ml of dimethyl sulfoxide. Evacuation to from 10 to 30 mbar is carried out, and 79.1 g of solvent are distilled off at from 80 to 100C. After establishing normal pressure, 24 g (content 94.9%) of 2-bromo-1, 3-diethyl-5-methylbenzene are added, and the reaction mixture is heated to 130C. At that temperature, a mixture of 0.13 g of TRIPHENYLPHOSPHINE, 0.1 g of a commercially available palladium (II) chloride solution in concentrated hydrochloric acid (20% Pd content corresponding to 0.035 g of palladium (li) chloride in 0.071 g of concentrated hydrochloric acid) and 9.6 g of 1-methyl-2-pyrrolidone is added. The reaction mixture is stirred for from 2 to 3 hours at from 125 to 140C. A further 59.5 g of solvent are distilled off at from 20 to 60 mbar. 1.5 g of Hyflo and 75 ml of water are added to the residue which has been cooled to 50C. The reaction mixture is stirred vigorously for 10 minutes and then clarified by filtration over Hyflo. The filter is then washed with 50 ml of water. 23.3 g of 32% hydrochloric acid are added to the filtrate in the course of from 60 to 80 minutes, at from 20 to 25C, during the course of which the product crystallises out and the pH value falls to from 4.0 to 4.5. Suction filtration is carried out, followed by washing with 100 ml of water (divided into 2 portions). The product is dried in a vacuum drying cabinet for 16 hours at from 100 to 250 mbar. 20.6 g (content 97.9% ; yield 95. 1%) of 2- (2, 6-diethyl-4-methylphenyl) malonic acid dinitrile are obtained.

The synthetic route of 314084-61-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; WO2004/50607; (2004); A1;,
Bromide – Wikipedia,
bromide – Wiktionary