5473-01-8 Archives - Ethers-buliding-blocks

New downstream synthetic route of 5473-01-8

The synthetic route of 5473-01-8 has been constantly updated, and we look forward to future research findings.

Related Products of 5473-01-8,Some common heterocyclic compound, 5473-01-8, name is 2-Bromo-6-methoxyaniline, molecular formula is C7H8BrNO, 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.

Step B: 2-Amino-3-bromophenol. To an ice cooled solution of 6-bromo-2-anisidine (1.01 g, 5 mmol) in methylene chloride (30 mL) was slowly added a 1.0 M solution of boron tribromide in methylene chloride (10 mL, 10 mmol) via syringe. The reaction was slowly warmed to room temperature and stirred overnight. Methanol (10 mL) was added and the solvents removed by rotoevaporation to give the title compound (0.87 g, 92percent yield).

The synthetic route of 5473-01-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck & Co., Inc.; US6291511; (2001); B1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Simple exploration of 2-Bromo-6-methoxyaniline

The synthetic route of 2-Bromo-6-methoxyaniline has been constantly updated, and we look forward to future research findings.

These common heterocyclic compound, 5473-01-8, name is 2-Bromo-6-methoxyaniline, 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. name: 2-Bromo-6-methoxyaniline

To a cooled (in an ice bath) suspension of 6-bromo-2-anisidine (63.52 g, 0.314 mol) in concentrated hydrochloric acid (130 ml) was added dropwise a solution of sodium nitrite (22 g, 0.32 mol) in water (100 ml) while the temperature was kept below 5 °C. After stirring for a further 30 min at 4 °C the red solution of the diazo compound was filtered and to the filtrate the chilled solution of tin(II) chloride dihydrate (175 g, 0.78 mol) in concentrated hydrochloric acid (200 ml) was added dropwise while occasionally adding water (all together ca. 500 ml water were added), while hydrazine hexachlorostannane precipitated. The reaction mixture was allowed to warm to room temperature and stirred for 3 h, after which the product was filtered off, and washed with saturated brine once. The solid was dissolved by the careful addition to a chilled aqueous solution of 25percent sodium hydroxide (200 ml) containing ca. 40 g of potassium tartrate. The product was extracted with dichloromethane (4 .x. 50 ml). The combined organic layers were washed with 2 M NaOH and water, dried over MgSO4 and evaporated to give 59.4 g (87percent) of desired product as a tan solid. Mass spectrum, m/z (I rel., percent): 219 (9), 218 (95), 217(10), 216 (100), 203 (64), 201(74), 200 (83), 198 (80), 186 (39).

The synthetic route of 2-Bromo-6-methoxyaniline has been constantly updated, and we look forward to future research findings.

The important role of 5473-01-8

The synthetic route of 5473-01-8 has been constantly updated, and we look forward to future research findings.

To a solution of 2-bromo-6-methoxyaniline (1.539 g, 7.62 mmol) in tetrahydrofuran (12 mL) was added 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (0.297 g, 0.364 mmol). Nitrogen was bubbled through the solution for about 3 minutes, then a 0.35 M in tetrahydrofuran solution of cyclobutylzinc(II) bromide (40 mL, 14.00 mmol) was added dropwise over 5 minutes. The reaction was stirred for 15 hours at ambient temperature. Additional cyclobutylzincbromide solution (24 mL) was added and the mixture was stirred at ambient temperature for 24 hours. The reaction was quenched with saturated aqueous ammonium chloride (50 mL), diluted with methyl tert-butyl ether (400 mL), and the layers were separated. The organic layer was concentrated in vacuo to give crude material that was purified via flash chromatography, eluting on a 40 g silica gel cartridge with 1-60percent methyl tert-butyl ether/hexanes over 40 minutes to provide the title compound. 1H NMR (501 MHz, chloroform-d) delta ppm 6.81 (ddd, J=7.5, 1.7, 0.8 Hz, 1H), 6.77 (t, J=7.7 Hz, 1H), 6.74 (dd, J=7.9, 1.8 Hz, 1H), 3.88 (s, 3H), 3.75 (d, J=17.6 Hz, 2H), 3.59-3.49 (m, 1H), 2.47-2.37 (m, 2H), 2.27-2.16 (m, 2H), 2.09 (tdt, J=10.5, 9.3, 7.9 Hz, 1H), 1.95-1.86 (m, 1H)+ MS (ESI+) m/z 178 (M+H)+.

The synthetic route of 5473-01-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AbbVie S.a.r.l.; Galapagos NV; Altenbach, Robert J.; Bogdan, Andrew; Couty, Sylvain; Desroy, Nicolas; Gfesser, Gregory A.; Housseman, Christopher Gaetan; Kym, Philip R.; Liu, Bo; Mai, Thi Thu Trang; Malagu, Karine Fabienne; Merayo Merayo, Nuria; Picolet, Olivier Laurent; Pizzonero, Mathieu Rafael; Searle, Xenia B.; Van der Plas, Steven Emiel; Wang, Xueqing; Yeung, Ming C.; (189 pag.)US2019/77784; (2019); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Introduction of a new synthetic route about 5473-01-8

Statistics shows that 2-Bromo-6-methoxyaniline is playing an increasingly important role. we look forward to future research findings about 5473-01-8.

5473-01-8, Name is 2-Bromo-6-methoxyaniline, 5473-01-8, belongs to ethers-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.

To a solution of 2-bromo-6-methoxyaniline (AK-90829) (1.000 mL, 7.55 mmol) in tetrahydrofuran (10 mL) was added Pd-PEPPSI-IPent-Cl (dichloro[1,3-bis(2,6-di-3-pentylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(II), 0.208 g, 0.242 mmol). Nitrogen was bubbled through the solution for about 3 minutes, then a 0.4 M in tetrahydrofuran solution of isopropylzinc(II) bromide (52 mL, 20.80 mmol) was added dropwise over 5 minutes, with nitrogen flushing through the system and the internal temperature rising slowly from 21¡ã C. to 32¡ã C. The reaction mixture was stirred for 15 hours at ambient temperature, at which point it was quenched with saturated aqueous ammonium chloride (50 mL), diluted with methyl tert-butyl ether (400 mL), and the layers were separated. The organic layer was filtered through a pad of silica gel and concentrated in vacuo. The crude material was purified via flash chromatography, eluting on a 40 g silica gel cartridge with 1-40percent ethyl acetate/heptanes over 40 minutes to provide the title compound. 1H NMR (400 MHz, chloroform-d) delta ppm 6.89-6.66 (m, 3H), 3.87 (s, 3H), 3.86 (s, 2H), 2.96 (hept, J=6.8 Hz, 1H), 1.28 (d, J=6.9 Hz, 6H)+

Statistics shows that 2-Bromo-6-methoxyaniline is playing an increasingly important role. we look forward to future research findings about 5473-01-8.