Tag: M.W=100-200

Application of 452-74-4, A common heterocyclic compound, 452-74-4, name is 1-Bromo-2-fluoro-4-methylbenzene, molecular formula is C7H6BrF, 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.

3-Fluoro-4-bromotoluene (5.0 g, 27 mmol) in carbon tetrachioride (50 mE) was treated with N-bromosuccinimide (7.0 g, 40 mmol, 1.5 eq) and heated to 80 C. Henzoyl peroxide (65 mg, 0.27 mmol, 0.01 eq.) was added and heating was continued for 1 h. The reaction was then cooled to ambient temperature and filtered, and the filtercake was washed sparingly with chloroform. The filtrate was washed with water and brine, dried over Na2SO4, and concentrated to give crude 3-fluoro-4-bromobenzyl bromide as a clear oil which was used without thrther purification.

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; INFINITY PHARMACEUTICALS, INC.; BEHNKE, Mark L.; CASTRO, Alfredo C.; EVANS, Catherine A.; GRENIER, Louis; GROGAN, Michael J.; LIU, Tao; SNYDER, Daniel A.; TIBBITTS, Thomas T.; US2015/368278; (2015); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 583-75-5, name is 4-Bromo-2-methylaniline, molecular formula is C7H8BrN, 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. Computed Properties of C7H8BrN

EXAMPLE 192 1,2-Dihydro-6-(3-nitrophenyl)-2,2,4,8-tetramethylquinoline (Compound 292, structure 86 of Scheme XXII, where R1 =R3-5 =H, R2 =nitro) 4-Bromo-2-methylaniline (5.58 g, 30 mmol) was treated with iodine (0.2 g, 0.9 mmol) and acetone (150 mL) in a sealed tube at. 80 C. for 24 h to provide 6-bromo-1,2-dihydro-8-methylquinoline (Compound 85 of Scheme XXII) in 9% yield as a yellow oil (0.70g). Most of the aniline (>80%) was recovered.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 583-75-5, its application will become more common.

Reference:
Patent; Ligand Pharmaceuticals Incorporated; US5696130; (1997); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 111721-75-6,Some common heterocyclic compound, 111721-75-6, name is 2-Bromo-3-fluoroaniline, molecular formula is C6H5BrFN, 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 stirred solution of 2-bromo-3-fluoro aniline (25.0 g, 131.57 mmol) in dichloromethane (500 mL) at 0 C under nitrogen was added acetic anhydride (18.65 mL, 197.36 mmol). The resulting mixture was warmed to room temperature and stirred for 16 hours. After that, the reaction mixture was diluted water and extracted with dichloromethane (2 x 500 mL). The combined organic phase was washed with brine, dried over anhydrous Na2S04 and concentrated in vacuo to get compound XlVa (crude), which was taken as such for the next step without further purification. Yield: 25 g, 81.91%. LC- MS Calc. for C8H7BrFNO, 232.05; Obs.; 232.0 [M+]; -NMR (300 MHz, DMSO-d6): delta 9.57 (s, 1H), 7.49-7.34 (m, 2H), 7.20-7.14 (m, 1H), 2.09 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Bromo-3-fluoroaniline, its application will become more common.

Reference:
Patent; BUGWORKS RESEARCH INDIA PVT LTD; PEER MOHAMED, Shahul Hameed; BHARATHAM, Nagakumar; KATAGIHALLIMATH, Nainesh; SHARMA, Sreevalli; NANDISHAIAH, Radha; RAMACHANDRAN, Vasanthi; VENKATARAMAN, Balasubramanian; (221 pag.)WO2018/225097; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 5433-01-2, name is 1-Bromo-3-isopropylbenzene, 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 5433-01-2, Product Details of 5433-01-2

A. (E)-3-(3-lsorhoropyl-phenyl)-propenal; 1-Btauomo-3-isopropylbenzene (14.5 g, 69 mmol), acrolein-diethylacetal (33.5 mL, 208 mmol), Bu4NOAc (44 g, 138 mmol), K2CO3 (14.5 g, 104 mmol), KCI (5.2 g, 70 mmol) and Pd(OAc)2 (0.5 g, 2 mmol) are suspended in 290 mL DMF and heated for 24 h at 900C. The reaction mixture is cooled to ambient temperature, diluted with water (10OmL) and acidified with 2N HCI. After extraction with TBME, the organic layer is washed with water, dried over Na2SO4, filtered and concentrated. The crude product is purified by flash chromatography on silica gel (eluent: hexane/AcOEt 19/1) to give the titie compound. TLC, Rf (hexane/AcOEt 10/1) = 0.56. MS(EI+): 175 (M+1).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2006/66896; (2006); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 10485-09-3, 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. 10485-09-3, name is 2-Bromoindene, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 9.49 g (48.7 mmol) of 2-bromo-lH-indene in 490 ml of ether, 12.3 g (46.3 mmol) of Zr(NMe2)4 was added. The reaction mixture was stirred for 12 h and then evaporated to dryness. The residue was dissolved in 500 ml of toluene, and 23.1 g (151 mmol) of bromotrimethylsilane was added. The mixture was stirred for 24 h at room temperature, evaporated to a volume equal to ca. 250 ml, and filtered through a glass frit (G4). Crystals that precipitated at a temperature of 3O0C from the filtrate were separated, washed with 3 x 20 ml of cold dichloromethane, and dried in vacuum. Yield 16.1 g (66%) of yellow crystalline product.Anal. calc. for C9H6Br4Zr: C, 20.59; H, 1.15. Found: C, 20.68; H, 1.20.1H NMR (CDCl3): delta 7.75 (dd, 2H, J = 6.5 Hz, J = 3.0 Hz, 5,6-H), 7.43 (dd, J = 6.5 Hz, J = 3.0 Hz, 2H, 4,7-H), 7.13 (s, 2H, 1,3-H).

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

Reference:
Patent; EXXONMOBIL CHEMICAL PATENTS, INC.; WO2007/70040; (2007); 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. 3814-30-0, name is (Bromomethyl)cyclopentane, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 3814-30-0

A mixture of Compound 74A (5 g, 30.6 mmol), (bromomethyl)cyclopentane (10 g, 61.3 mmol), and C52CO3 (30 g, 92 mmol) in DMF (100 mL) was stirred at room temperature for 18 hours. The reaction mixture was treated with H20 (50 mL) and ethyl acetate (50 mL), washed with water (500 mL x 3), dried over anhydrous sodium sulfate, filtered, and concentrated. The crude product was purified by silica gel column chromatography to furnish Compound 74B and Compound 74C.Compound 74B: LC-MS (ESI) m/z: 246 [M+H] ?H-NMR (CDC13, 400 IVIHz): (5(ppm) 1.30-1.31 (m, 2H), 1.57-1.60 (m, 2H), 1.58-1.78 (m, 4H), 2.55-2.59 (m, 1H), 4.39 (d, J 7.6 Hz, 2H), 7.75 (d, J 9.6 Hz, 1H), 8.10 (d, J= 9.6 Hz, 1H), 8.21 (s, 1H), 8.73 (s, 1H). Compound 74C: LC-MS (ESI) m/z: 246 [M+H] ?H-NIVIR (CDC13, 400 IVIHz): (5(ppm) 0.80-0.89 (m, 2H), 1.26-1.36 (m, 2H), 1.60-1.78 (m, 4H), 2.63-2.65 (m, 1H), 4.39 (d, J 7.6 Hz, 2H), 7.75 (d, J 9.6 Hz, 1H), 8.10 (d, J= 9.6 Hz, 1H), 8.21 (s, 1H), 8.73 (s, 1H).

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; BIOMARIN PHARMACEUTICAL INC.; WANG, Bing; (377 pag.)WO2018/118838; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 17247-58-4, name is (Bromomethyl)cyclobutane, 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 17247-58-4, Product Details of 17247-58-4

To a stirred solution of 14 (100 mg, 0.32 mmol) in DMF (1 mL) were added K2CO3 (310 mg, 2.22 mmol) and (bromomethyl)cyclobutane (150 muL, 1.27 mmol), and stirred at 60 C under an Ar atmosphere. After 24 h with stirring, the reaction mixture was evaporated in vacuo. The resulting mixture was basified (pH 9) with saturated NaHCO3 aqueous solution and extracted with CHCl3 three times. The combined organic extracts were washed with brine, dried over Na2SO4, and evaporated in vacuo. The residue was purified by preparative TLC (CHCl3/MeOH = 10/1) to give 17 (79 mg, 65%) as a colorless oil. IR (neat): 2936, 1611, 1497 cm-1; 1H NMR (CDCl3, 400 MHz) delta: 1.30-1.38 (1H, m), 1.40-1.53 (2H, m), 1.57 (1H, d, J = 14.4 Hz), 1.60-1.92 (8H, m), 1.93-2.12 (3H, m), 2.40-2.62 (5H, m), 2.63 (1H, dd, J = 6.4, 18.0 Hz), 2.92-2.98 (1H, m), 2.94 (1H, d, J = 18.0 Hz), 3.72-3.79 (1H, m), 3.76 (3H, s), 3.80-3.86 (2H, m), 3.89-3.96 (1H, m), 6.68 (1H, dd, J = 2.8, 8.4 Hz), 6.81 (1H, d, J = 2.8 Hz), 6.98 (1H, d, J = 8.4 Hz). MS (ESI) m/z = 384 [M+H]+. HRMS (ESI) Calcd for C24H34NO3 [M+H]+: 384.2539. Found 384.2548.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; Ida, Yoshihiro; Nemoto, Toru; Hirayama, Shigeto; Fujii, Hideaki; Osa, Yumiko; Imai, Masayuki; Nakamura, Takashi; Kanemasa, Toshiyuki; Kato, Akira; Nagase, Hiroshi; Bioorganic and Medicinal Chemistry; vol. 20; 2; (2012); p. 949 – 961;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 630-17-1, name is 1-Bromo-2,2-dimethylpropane, 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 630-17-1, Quality Control of 1-Bromo-2,2-dimethylpropane

Intermediate 7A: 6-{(E)-2-[3-(Difluoromethoxy)-2-(2,2-dimethylpropoxy)phenyl]vinyl}imidazo[2,1-b][1,3]thiazole-5-carboxylic acid; Step 1 Ethyl 6-{(E)-2-[3-(difluoromethoxy)-2-(2,2-dimethylpropoxy)phenyl]vinyl}imidazo[2,1-b][1,3]thiazole-5-carboxylate: To a stirred solution of Intermediate 6 (1.60 g, 4.209 mmol) in anhydrous N,N-dimethylformamide (10 mL) was added cesium carbonate (2.74 g, 8.418 mmol) followed by 1-bromo-2,2-dimethylpropane (1.60 mL, 12.629 mmol) at room temperature. The resulting suspension was stirred at 110 C. overnight under nitrogen atmosphere. The reaction mixture was cooled to room temperature and diluted with ethyl acetate (200 mL) and water (100 mL). The layers were separated. Aqueous layer was extracted with ethyl acetate (2×50 mL) and the combined organic layers were washed with brine (2×50 mL), dried (Na2SO4) and filtered. The filtrate was concentrated under reduced pressure. The residue obtained after the evaporation of the solvent was purified by silica gel column chromatography using 10% ethyl acetate in petroleum ether to obtain 1.20 g of the product as an off-white solid; 1H NMR (300 MHz, DMSO-d6) delta 1.07 (s, 9H), 1.39 (t, J=6.9 Hz, 3H), 3.57 (s, 2H), 4.35-4.42 (m, 2H), 7.18 (t, J=74.7 Hz, 1H), 7.20-7.25 (m, 2H), 7.47 (d, J=3.9 Hz, 1H), 7.52-7.58 (m, 1H), 7.73 (d, J=16.2 Hz, 1H), 7.90 (d, J=16.2 Hz, 1H), 8.10-8.16 (m, 1H); APCI-MS (m/z) 451.10 (MH)+.

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

Reference:
Patent; Glenmark Pharmaceuticals S.A; US2010/152192; (2010); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 1073-06-9, 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. 1073-06-9, name is 1-Bromo-3-fluorobenzene, This compound has unique chemical properties. The synthetic route is as follows.

Magnesium chips (13.2 g) were placed into a 1L flask equipped with mechanical stirrer, nitrogen inlet, 500 ml pressure-equilibrated dropping funnel, thermometer and reflux condenser connected to the inert gas outlet. The flask was flushed with nitrogen and minor flow was held during whole reaction time. 1-Bromo-3-fluorobenzene (95 g, 0.542 mol) and dry tetrahydrofurane (300 ml) was placed in dropping funnel. Magnesium was moistened with few milliliters of the solution from dropping funnel and an iodine crystal was added. When exothermic reaction starts 1-bromo-3-fluorobenzene solution was added dropwise to keep the boiling temperature of the mixture. After dropping all of the solution, the mixture was refluxed for 2 hours. Then the mixture was cooled down to -78 C. in a dry ice/acetone bath and propionaldehyde was added dropwise while mixture temperature was kept below -70 C. After adding all of the aldehyde, the mixture was left overnight at room temperature. Then the tetrahydrofurane was evaporated and the residue was acidified with hydrochloric acid. The organic phase was separated, washed twice with water and dried over magnesium sulfate. The raw 1-(3-fluorophenyl)propanol was distilled under reduced pressure of 20 mbar at 117 C. Alcohol 60 g, 66% of theor. yield was obtained. The alcohol and toluene (250 ml) and p-toluenesulfonic acid (0.2 g) were placed in (500 ml) round-bottom flask equipped with Dean-Stark trap. The mixture was refluxed. After the water stopped appearing, toluene was evaporated at reduced pressure. The obtained 1-(3-fluorophenyl)propene was placed in a three-necked flask and acetic acid (30 ml), ethyl acetate (50 ml) and catalyst-palladium on active carbon (2 g) were added. The flask was filled with hydrogen from gas burette at room temperature and the mixture was stirred. Reaction temperature increased spontaneously to 30 C. When the absorption of hydrogen was stopped, the catalyst was filtered off, the solution was washed off with water, dried over MgSO4 and the solvent was evaporated. The 1-fluoro-3-propylbenzene was distilled under atmospheric pressure, collecting the fraction boiling at 160 C. 32 g of 1-fluoro-3-propylbenzene were obtained, 42% of theor. yield.

The chemical industry reduces the impact on the environment during synthesis 1-Bromo-3-fluorobenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Dabrowski, Roman Slawomir; Kula, Przemyslaw; Choluj, Artur; Dziaduszek, Jerzy; Garbat, Katarzyna; US2013/20532; (2013); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 74586-53-1, The chemical industry reduces the impact on the environment during synthesis 74586-53-1, name is 3-Bromo-5-methylaniline, I believe this compound will play a more active role in future production and life.

To a stirring solution of 3-bromo-5-methylaniline (5.00 g, 26.9 mmol) in THF (100 mL) was added K2CO3 (11.14 g, 81 mmol) followed by 2-chloroethyl chloroformate (4.16 mL, 40.3 mmol) and the resulting reaction mixture was refluxed for 4 h. The reaction mixture was cooled to ambient temperature, diluted with 5% NaHCO3 solution (100 mL) and extracted with ethyl acetate (2 x 100 mL). The combined organic layers were washed with brine (50 mL), dried over anhydrous sodium sulfate and evaporated under reduced pressure to obtain Intermediate 76A (7.00 g, 89.00%) as a white solid. 1H NMR (300 MHz, DMSO-d6) G^ppm 2.25 (s, 3 H), 3.81 – 3.95 (m, 2 H), 4.32 – 4.42 (m, 2 H), 7.04 (s, 1 H), 7.26 (s, 1 H), 7.55 (s, 1 H), 9.96 (s, 1 H). LCMS (Method-D ): retention time 2.99 min, [M+H] 291.0.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 3-Bromo-5-methylaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; YADAV, Navnath Dnyanoba; BHIDE, Rajeev S.; BORA, Rajesh Onkardas; GUNAGA, Prashantha; PANDA, Manoranjan; PRIESTLEY, Eldon Scott; RICHTER, Jeremy; (444 pag.)WO2018/222795; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary