Sodium Carbonate → 2-Chloro-4-benzylnitrobenzene

Participants

Reaction Steps

Sodium borohydride (1.45 g) was added to a solution of 3-chloro-4-nitrobenzophenone (2.0 g) (prepared as described by R. B. Davis and J. D. Benigni, J. Org. Chem., 1962. 27, 1605) in ethanol and the mixture was stirred for 18 hours. Volatile material was removed by evaporation and the residue was suspended in water (100 ml) and cautiously acidified with dilute aqueous hydrochloric acid (50 ml) and stirred a further 2 hours. The reaction mixture was basified with 2M aqueous sodium hydroxide solution and extracted with DCM. The extracts were combined, dried and concentrated by evaporation to give an oil. This was dissolved in TFA (12.1 ml) with cooling with an ice bath then treated dropwise with triethylsilane (5.05 ml) and stirred overnight. The reaction mixture was poured onto aqueous sodium carbonate solution and extracted with DCM. The extracts were combined, dried and evaporated to give an oil which was purified by chromatography eluting with 20-50% ethyl acetate/hexane to give the title compound (0.60 g) as an oil. NMR (CDCl3): 4.0 (s, 3H), 7.1-7.4 (m, 8H); MS (CI): 247 (M+).

Provenance & Evidence