[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([Br:9])=[C:6]([OH:8])[CH:7]=1.CC(C)([O-])C.[K+].[CH2:16](Cl)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[Na]>CN(C)C=O>[CH2:16]([O:8][C:6]1[CH:7]=[C:2]([NH2:1])[CH:3]=[CH:4][C:5]=1[Br:9])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1To a solution of 5-amino-2-bromo-phenol (35.2 g, 0.187 mol) in N,N-dimethylformamide (350 mL) was added potassium tert-butoxide (22.9 g, 0.204 mol). After 15 min, benzyl chloride (25.5 mL, 0.222 mol) was added within 2 min. The reaction was stirred during 4 h and then poured onto an aqueous solution of sodium hydrogenocarbonate and extracted with ethyl acetate. The combined organic phases were washed with brine and water then dried over sodium sulfate, filtered, and evaporated under vacuum. 55.6 g of the title compound were obtained. Black solid, ISP-MS: m/e=279.1 ([M+H]+).
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