Benzyl Bromide → 2-Benzyloxy-6-nitroaniline

Participants

Reaction Steps

6.16 g (40 mM) of 2-amino-3-nitrophenol, 60 ml of dimethylformamide and 6.62 g (48 mM) of dipotassium carbonate are introduced into a round-bottomed flask. 4.75 ml (40 mM) of benzyl bromide are then added dropwise and the reaction mixture is brought to 80° C. After havingbeen stirred under an inert atmosphere for 1.5 hours, the mixture is pouredinto ice-cold water and then extracted with 200 ml of ethyl acetate. The organic phase is separated by settling and, after washing with a saturatedsodium chloride solution, it is dried over magnesium sulphate and evaporated to dryness. The product is chromatographed on a silica column (eluent: 10% ethyl acetate and 90% hexane) to lead to 8.8 g (90%) of the expected compound in the form of an orangey oil.

Provenance & Evidence