168268-00-6

76243-24-8

168268-00-6

General procedure for the synthesis of 4-(benzyloxy)-3-fluoroaniline from 1-benzyloxy-2-fluoro-4-nitrobenzene: a mixture of iron powder (45.2 g, 0.809 mol), ammonium formate (53.6 g, 0.550 mol), 1-benzyloxy-2-fluoro-4-nitrobenzene (50.0 g, 0.200 mol), and toluene (400 g) was mixed with deionized water (400 mL) was heated to reflux and reacted overnight. Upon completion of the reaction, the mixture was filtered through diatomaceous earth and the filter cake was washed with hot ethyl acetate. The organic layers were combined, washed sequentially with water and saturated saline, and then dried over anhydrous sodium sulfate. The organic phase was concentrated under reduced pressure to give 4-(benzyloxy)-3-fluoroaniline (44 g, 100% yield).