Category: bromides-buliding-blocks

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. 3814-30-0, name is (Bromomethyl)cyclopentane, This compound has unique chemical properties. The synthetic route is as follows., Formula: C6H11Br

A solution of diethyl malonate (36.91 g, 230.4 mmol), anhydrous methanol (400 mL), and NaOMe (25% in methanol, 49.79 g, 230.4 mmol) is stirred at reflux for one hour under nitrogen. Bromomethyl-cyclopentane (31.31 g, 192.0 mmol) is added to the mixture, and stirred for an additional 3 hours. A solution of NaOH (23.04 g, 576.0 mmol) in water (400 mL) is added, and the mixture is stirred for an additional 1 hour at reflux. The mixture is cooled, diluted with water, and extracted with ether. The ether layer is discarded, and the aqueous layer is acidified with 1N HCl to pH=1. The aqueous layer is extracted with EtOAc. The EtOAc layers are combined, dried over Na2SO4, and concentrated. This gives 2-cyclopentylmethyl-malonic acid (21.0 g, 59% yield) as a white solid.

According to the analysis of related databases, 3814-30-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Lee, Kwangho; Leeds, Jennifer A.; US2009/62537; (2009); A1;,
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In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 52548-00-2, name is 1-Bromo-4-fluoro-2,3-dimethylbenzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C8H8BrF

Step a. To a solution of 3-bromo-6-fluoro-o-xylene (CAS Number 52548-00-2; 3.00 g, 14.8 mmol) in CC1 (45 ml) was added NBS (5.780 g, 32.51 mmol) at rt. The reaction mixture was exposed to a UV light source which increased the temperature, in this manner the reaction mixture was heated at 85C for 2 h. The reaction mixture was cooled to rt and poured into saturated NaHC03 solution (100 ml). The resulting mixture was extracted with EtOAc (3 x 100 ml). The combined organic phase was washed with brine (100 ml), dried over Na2S04, filtered and concentrated under reduced pressure yielding 1-bromo-2,3-bis(bromomethyl)-4-fluorobenzene (5.80 g, 16.25 mmol). This material was directly used for next step without any further purification. LCMS: Method A, 2.489 min.

The synthetic route of 52548-00-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MISSION THERAPEUTICS LIMITED; GIBSON, Karl Richard; JONES, Alison; KEMP, Mark Ian; MADIN, Andrew; STOCKLEY, Martin Lee; WHITLOCK, Gavin Alistair; WOODROW, Michael D; (241 pag.)WO2017/158388; (2017); A1;,
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Related Products of 24358-62-1, These common heterocyclic compound, 24358-62-1, name is 1-(4-Bromophenyl)ethylamine, 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: (R)-1-(4-bromophenyl)ethanamine (2b) (2.00g, 10.0mmol) was dissolved in MeOH (50mL). To this solution was added 1-butanal (1.78mL, 20.0mmol) and NaBH(OAc)3 (4.24g, 20.0mmol). After stirring for 18h at room temperature, 5% NaOH was added. The mixture was extracted with CHCl3, dried over MgSO4, filtered, and concentrated under reduced pressure. The crude material was purified by silica gel column chromatography eluted with 5-10% MeOH in CHCl3 to afford the titled compound (2.17g, 85%) as a colorless oil. 1H NMR (400MHz, CDCl3) delta: 7.44 (d, J=8.8Hz, 2H), 7.19 (d, J=8.8Hz, 2H), 3.72 (q, J=6.8Hz, 1H), 2.50-2.44 (m, 1H), 2.41-2.34 (m, 1H), 1.47-1.38 (m, 2H), 1.35-1.24 (m, 5H), 0.87 (t, J=7.3Hz, 3H). 13C NMR (100MHz, CDCl3) delta: 143.5, 131.6(2C), 128.5(2C), 120.8, 57.9, 47.2, 31.7, 23.7, 20.3, 13.9. LC-MS (ESI) m/z=256 [M+H]+.

The synthetic route of 24358-62-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Imaizumi, Takamichi; Kobayashi, Atsuko; Otsubo, Shigeki; Komai, Masato; Magara, Megumiko; Otsubo, Nobumasa; Bioorganic and Medicinal Chemistry; vol. 27; 21; (2019);,
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Related Products of 54962-75-3,Some common heterocyclic compound, 54962-75-3, name is 3-Bromo-5-(trifluoromethyl)aniline, molecular formula is C7H5BrF3N, 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.

3-(1H-imidazo1-1-y1)-5-(trfluoromethy1)anh1ine: A mixture of 3-Amino-5- bromobenzotrifluoride (4.0 g, 0.0167 mol), 8-hydroxy quinoline (0.362 g, 0.0025 mol), Cul (0.476 g, 0.025 mol), irnidazole (1.36 g, 0.0199 mol), and potassium carbonate (2.52 g, 0.0183mol) in 17 mL of DMSO (degassed with argon for 10 mm) was heated at 120C under an atmosphere of argon for 15 h; the HPLC indicated no starting material. A 14% aqueous solution of ammonium hydroxide was added to the cooled mixture and this was stirred for I h at ambient temperature. Water (50 mL) and EtOAc (200 mL) were added and the aqueous layer was extracted with EtOAc (3x3OmL). The combined organic layers were dried over Na2SO4 andconcentrated, The crude product was purified by silica gel flash chromatography (eluted with EtOAc/hexanes) to provide 2.51 g of product.

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-5-(trifluoromethyl)aniline, its application will become more common.

Reference:
Patent; ARIAD PHARMACEUTICALS, INC.; GOZGIT, Joseph, M.; RIVERA, Victor, M.; SHAKESPEARE, William, C.; ZHU, Xiaotian; DALGARNO, David, C.; WO2013/162727; (2013); A1;,
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Electric Literature of 2550-36-9, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 2550-36-9, name is (Bromomethyl)cyclohexane belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: 2,6-Dihydroxyacetophenone 7 (1.0equiv.) was dissolved in acetone (10mL) and then anhydrous potassium carbonate (2.0equiv.) with corresponding alkyl bromides (1.0equiv.) were added and the reaction mixture was stirred at 80C for overnight. After evaporating the solvent under reduced pressure the reaction mixture was further diluted with dichloromethane (20mL) and washed with water (20mL×3). The organic layer was dried over anhydrous sodium sulfate and evaporated under reduced pressure. The crude product was purified by flash column chromatography to afford the title compounds 8. 6.1.1.1 1-(2-(Cyclohexylmethoxy)-6-hydroxyphenyl)ethanone (8a) Yield 50%; Yellow colored solid; 1H NMR (CDCl3) delta 13.20 (s, 1H), 7.29 (t, J = 8.4 Hz, 1H), 6.53 (d, J = 8.4 Hz, 1H), 6.40 (d, J = 8.4 Hz, 1H), 3.81 (d, J = 6.0, 2H), 2.72 (s, 3H), 1.69-1.87 (m, 5H), 1.19-1.29 (m, 6H).

The synthetic route of (Bromomethyl)cyclohexane has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yang, Hyun-Sun; Venkateswararao, Eeda; Boggu, Pulla Reddy; Sharma, Vinay K.; Kim, Youngsoo; Jung, Sang-Hun; Bioorganic and Medicinal Chemistry; vol. 25; 16; (2017); p. 4330 – 4338;,
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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. 766-81-4, name is 3-Bromophenylacetylene, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 3-Bromophenylacetylene

Step B: 4-[(3-Bromophenyl)ethynyl]-2-chloro-5-fluoropyrimidine; To an oven-dried flask under N2 was added 2,4-dichloro-5-fluoropyrimidine (1.66 g, 10 mmol), anhydrous, degassed THF (100 mL), dichlorobis(triphenyl-phosphine)palladium(II) (180 mg, 0.26 mmol), copper(I) iodide (29 mg, 0.15 mmol), and TEA (2.02 g, 20 mmol). After heating the reaction at 60 C. for 30 min, 1-bromo-3-ethynylbenzene (0.9 g, 5.0 mmol) was added dropwise as a solution in THF (25 mL) and the resulting mixture was allowed to heat overnight. The crude reaction mixture was adsorbed to silica gel and purified by column chromatography (2-10% EtOAc in hexanes) to afford the desired product (1.25 g, 78%) as an off white solid. ESIMS (M+H)+=311.

According to the analysis of related databases, 766-81-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SmithKline Beecham Corporation; US2008/51395; (2008); A1;,
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Application of 112734-22-2, These common heterocyclic compound, 112734-22-2, name is (4-Bromo-2-fluorophenyl)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.

Boc20 (106.96 mg, 490.10 muiotaetaomicron) and DMAP (5.99 mg, 49.01 muiotaetaomicron) were added to a solution of Compound BD2-2 (100.00 mg, 490.10 muiotaetaomicron) and TEA (148.78 mg, 1.47 mmol) in DCM (4.00 mL). The mixture was stirred at 15C for 12 hours. LCMS showed the reaction was completed. The mixture was concentrated to get crude residue. The residue was purified by prepatory-TLC (S1O2, Petroleum ether:Ethyl acetate mixture with a ratio of 5: 1) to afford Compound BD2-3 (90.00 mg, crude) as a yellow oil.

Statistics shows that (4-Bromo-2-fluorophenyl)methanamine is playing an increasingly important role. we look forward to future research findings about 112734-22-2.

Reference:
Patent; THE BROAD INSTITUTE, INC.; VACCA, Joseph, P.; (103 pag.)WO2018/75871; (2018); A1;,
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Some common heterocyclic compound, 80058-84-0, name is 4-Bromo-2,6-diisopropylaniline, molecular formula is C12H18BrN, 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. Recommanded Product: 4-Bromo-2,6-diisopropylaniline

138 ml (2.59 mol) of96percent sulfuric acid was added dropwise to a solution of 4-bromo-2,6-diisopropylaniline (as prepared above, purity ca. 90percent) in 2000 ml of95percent ethanol cooled to -1 ooc at such a rate to keep the reaction temperature below 7°C. After the addition was complete, the formed solution was stirred at roomtemperature for 1 h. Then, the reaction mixture was cooled in an ice-bath, and asolution of 103.1 g (1.49 mol) of sodium nitrite in 215 ml of water was addeddropwise over ca. 1 h. The formed solution was stirred at the same temperature for30 min. Further on, the cooling bath was removed, and 18 g of copper powder was added. Upon completion of the rapid evolution of nitrogen additional portions (ca. 5g each, ca. 70 gin total) of copper powder were added with 10 min intervals untilgas evolution ceased completely. The reaction mixture was stirred at roomtemperature overnight, then filtered through glass frit (G3), diluted with two-foldvolume of water, and crude product was extracted with 4 x 200 ml of dichloromethane. The combined extract was dried over K2C03, evaporated todryness, and then distilled in vacuum (b.p. up to 120°C/5 mm Hg) to give ayellowish liquid. This product was additionally purified by flash-chromatography onsilica gel 60 ( 40-63 )lm; eluent: hexane) and distilled once again (b.p. 85-99°C/5mm Hg) to give 120.0 g (52percent) of 1-bromo-3,5-diisopropylbenzene as a colorless liquid.1H NMR (CDCh): b 7.19 (d, J = 1.2 Hz, 2H), 6.99 (br.t, 1H), 2.86 (sept, J = 6.9 Hz,2H), 1.24 (d, J= 6.9 Hz, 12H). 13CeH} NMR (CDCh): b 151.04, 126.85, 123.70,122.34, 34.06, 23.87

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 80058-84-0, its application will become more common.

Reference:
Patent; BOREALIS AG; AJELLAL, Noureddine; RESCONI, Luigi; IZMER, Vyatcheslav V.; KONONOVICH, Dmitry S.; OSKOBOYNIKOV, Alexander Z.; VIRKKUNEN, Ville; (133 pag.)WO2018/91684; (2018); A1;,
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Application of 112279-60-4, 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. 112279-60-4, name is 4-Bromo-2,5-difluoroaniline, This compound has unique chemical properties. The synthetic route is as follows.

A degassed solution of ethyl 3-(nonafluorobutane-l-sulfonyloxy)-furo[3,2- c]pyridine-2-carboxylate (500 mg, 1.02 mmol), 4-bromo-2,5-difluoroaniline (277 mg, 1.33 mmol), Pd2dba3 (47 mg, 0.05 mmol), Xantphos (59 mg, 0.10 mmol) and DBU (388 mul, 2.56 mmol) in toluene (2.0 ml) was subjected to microwave irradiation at 15O0C for 10 minutes. The reaction mixture was concentrated and the resultant residue absorbed onto HM-N before being purified by flash chromatography (Si-SPE, cyclohexane: ethyl acetate, gradient 100:0 to 0: 100) to afford the title compound as a white solid (231 mg, 57%). LCMS (method B): Rx = 3.22 min, M+H+ = 397/399.

The chemical industry reduces the impact on the environment during synthesis 4-Bromo-2,5-difluoroaniline. I believe this compound will play a more active role in future production and life.

Reference:
Patent; GENENTECH, INC.; WO2008/24725; (2008); A1;,
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Related Products of 86845-27-4, These common heterocyclic compound, 86845-27-4, name is 5-Bromo-2-methylbenzotrifluoride, 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.

To a solution of 4-Bromo-1-methyl-2-trifluoromethyl-benzene (3.4 g, 14.2 mmol) in THF was added n-BuLi at -78 C. After the reaction mixture was stirred at -78 C. for 30 minutes, dry acetone was slowly added. The resulting content was maintained at -78 C. for 3 hours and slowly warmed up to RT overnight. The reaction mixture was then partitioned between ethyl acetate and water. The ethyl acetate layer was then washed with brine, dried over Na2SO4, filtered, and the solvent evaporated in vacuo to yield a crude oil. The crude solid was purified via flash chromatography (15% EtOAc in n-hexane) yielded the title compound as an oil (2.7 g, 86%).1H NMR (400 MHz, CDCl3) delta 7.73 (d, 1H), 7.53 (dd, 1H), 7.25 (d, 1H), 2.47 (q, 3H), 1.58 (s, 6H).

Statistics shows that 5-Bromo-2-methylbenzotrifluoride is playing an increasingly important role. we look forward to future research findings about 86845-27-4.

Reference:
Patent; BIGNAN, Gilles; Gaul, Micheal; Xu, Guozhang; Zhao, Bao-Ping; US2011/150864; (2011); A1;,
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