Anisole → HCID 19354606, compound

Participants

Reaction Conditions

Reaction Steps

A solution of aluminium tribromide (3.85 g) in nitromethane was added in portions to a stirred solution of benzyl 2-(6-difluoromethyl-2,3-dihydro-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanoate (1.93 g) and anisole (3.1 g) in dichloromethane at 0° C. under an inert atmosphere. The reaction mixture was stirred at 0° C. for 10 minutes and at ambient temperature for 2 hours and diluted with dichloromethane. The dichloromethane solution was washed in turn with 2 M hydrochloric acid and with water. The organic solution was extracted with 1 M sodium bicarbonate, the aqueous extract was then washed with diethyl ether and acidified to pH 1 with 2 M hydrochloric acid. The acidic solution was extracted with ethyl acetate, the extract was dried (magnesium sulphate) and evaporated under reduced pressure to give 2-(6-difluoromethyl-2,3-dihydro-4-oxo-5-phenyl-4H-1, 3-oxazin-3-yl)-2-methylpropanoic acid (0.70 g) as a pink solid, m.p. 149-151° C.

Provenance & Evidence