O.[Sn](Cl)Cl.[CH2:5]([O:8][C:9]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:10]=1[N+:16]([O-])=O)[CH:6]=[CH2:7].C(N(CC)CC)C>C(OCC)(=O)C>[CH2:5]([O:8][C:9]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:10]=1[NH2:16])[CH:6]=[CH2:7]Tin (II) chloride hydrate (8.5 g, 38 mmol, 5 eq) was added to a solution of 2-allyloxy-4-fluoro-1-nitro-benzene (1.5 g, 7.6 mmol) in ethyl acetate (20 ml) at room temperature and the mixture was stirred for 4 hr. The reaction mixture was neutralized with triethylamine and then partitioned between water and ethyl acetate. The organic layer was separated, dried over anhydrous sodium sulfate, filtered and concentrated to dryness to give 2-allyloxy-4-fluoro-phenylamine (0.6 g, 50%). The crude compound was used in the next stage without purification.
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