Stannous chloride dihydrate → 3-(Benzyloxy)-5-bromoaniline

Participants

Reaction Steps

To a solution of 1-benzyloxy-3-bromo-5-nitro-benzene (551 g, 1.78 mol) in THF (11 L) was added SnCl2.2H2O (2.17 kg, 9.62 mol) in one portion at rt. The reaction mixture was refluxed for 3 h. After completion of reaction (by TLC) the reaction mixture was cooled to 0-5° C. and basified with saturated NaHCO3 solution then extracted with EtOAc (4×5 L). The combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to obtain a crude liquid product (480 g, 97%) that was carried forward to the next step without further purification.

Provenance & Evidence