Benzyl Bromide → Benzyl 2-(benzyloxy)-4-chlorobenzoate

Participants

Reaction Conditions

Reaction Steps

To a solution of 7.0 g (40.6 mmol) 2-hydroxy-4-chlorobenzoic acid in 150 ml of dry DMF was added 16.8 g (122 mmol) of K2CO3 followed by the dropwise addition of 15.2 g (89.2 mmol) of benzyl bromide. The reaction mixture was warmed to 50° C. and stirred overnight. After 16h, the reaction mixture was diluted with Et2O and H2O and the layers were separated. The aqueous layer was extracted with Et2O (2×) and the combined organic layers were successively washed with 1N HCl (3×100 ml), saturated NaHCO3 solution (2×50 ml) and brine (1×50 ml). The solution was dried over anhydrous MgSO4 and concentrated to give 2-benzyloxy-4-chlorobenzoic acid, benzyl ester as a pale yellow solid which was used without further purification.

Provenance & Evidence