Benzyl Bromide → 4-(Benzyloxy)-2-methyl-6-nitroaniline

Participants

Reaction Steps

0.84 g (5.00 mmol) 4-amino-3-methyl-5-nitrophenol was placed in 10 mL DMF, combined with 0.78 g (5.50 mmol) potassium carbonate and stirred for 10 min at RT. Then 0.65 mL (5.50 mmol) benzylbromide were added and the mixture was stirred for a further 30 min at RT and for 1 h at 60° C. Another 0.33 mL benzylbromide were added and the mixture was stirred for 1 h at 60° C. The reaction mixture was poured onto ice water, extracted with ethyl acetate and evaporated down i.vac. The residue was purified by chromatography. The fractions containing product were combined and evaporated down i.vac. to leave the aqueous residue. This was neutralised with a 1M aqueous NaOH solution and extracted with ethyl acetate. The organic phase was evaporated down i.vac.

Provenance & Evidence