19056-40-7, These common heterocyclic compound, 19056-40-7, name is 4-Bromo-3-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.
Under an atmosphere of nitrogen, in a 100 mL round-bottomed flask at 0¡ã C., 4-bromo-3-methoxyaniline (2 g, 9.9 mmol) and KOH (6.93 ml, 13.9 mmol) were combined with dichloromethane (30 ml) to give a light brown solution. Then 4-bromobutanoyl chloride (1.84 g, 1.15 ml, 9.9 mmol) was added. The reaction was stirred for 1 h at RT. The reaction mixture was poured into 50 ml dichloromethane and extracted with water (3*20 ml). The organic layer was dried over Na2SO4 and concentrated in vacuo. The residue was dissolved in 30 ml dichloromethane. Then tetrabutylammonium bromide (63.8 mg, 198 mumol) and KOH (50percent, 6 ml) were added. The reaction was stirred for 1 h at RT. The reaction mixture was poured into dichloromethane (50 ml) and extracted with water (3*20 ml). The organic layers were dried over Na2SO4 and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 50 g, 20percent to 50percent EtOAc in heptane). The title compound was obtained as a off-white crystalline (1.92 g, 71.8percent). MS (m/e)=272.1 [M+H]+.
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 19056-40-7.
Reference:
Patent; Hoffmann-La Roche Inc.; Jakob-Roetne, Roland; Wichmann, Juergen; Peters, Jens-Uwe; Jagasia, Ravi; (33 pag.)US2016/326150; (2016); A1;,
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