Ethanol → tert-Butyl 4-[5-bromo-2-benzyloxybenzylamino]benzoate

Participants

Reaction Steps

5-Bromo-2-benzyloxybenzoic acid [International patent application, publication no, WO 96/03380] and tert-butyl-4-aminobenzoate were heated on a steam bath for 2 hours. Ethanol (50 ml) and tetrahydrofuran (50 ml) were added to the hot reaction mixture. The solution was allowed to cool and sodium borohydride (1.4 g) was added. The reaction mixture was then stirred at ambient temperature for 3 hours, poured into water (200 ml) and extracted with dichloromethane (4×100 ml). The combined extracts were dried over magnesium sulphate to give tert-butyl 4-[5-bromo-2-benzyloxybenzylamino]benzoate which was used without further purification (18 g).

Provenance & Evidence