[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].C(=O)([O-])O.[Na+].O.[Br:15][CH:16]([CH:20]([CH3:22])[CH3:21])[C:17](Cl)=[O:18]>C(OCC)(=O)C>[Br:15][CH:16]([CH:20]([CH3:22])[CH3:21])[C:17]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8])=[O:18]To a mixture of 2-aminophenol (27 25 g), sodium hydrogencarbonate (31.5 g), ethyl acetate (250 ml), and water (200 ml), a solution of 2-bromo-3-methylbutyryl chloride (49.8 g) in ethyl acetate (100 ml) was added dropwise with ice-cooling and with stirring. After stirring with ice-cooling for further 1 hour, the ethyl acetate layer was separated, washed with water, and dried (MgSO4), and the solvent was evaporated off. The residue was crystallized from hexane, to give 2-(2-bromo-3-methylbutyryl)aminophenol. Yield was 59.7 g (87.9%). Recrystallization from isopropyl ether gave colorless prisms, mp 110°-111° C.
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