Benzyl Bromide → Benzyl-2,4-bis-benzyloxy-5-bromobenzoate

Participants

Reaction Steps

The mixture of 2,4-dihydroxy-5-bromobenzoic acid (23.3 g, 0.1 mol), BnBr (54 g, 0.33 mol) and excess K2CO3 (80 g, 0.58 mol) was stirred in acetone (500 ml) at 85° C. overnight. HPLC indicated the completion of the reaction. After cooling to r.t, the reaction was filtered, and the filtrate was concentrated to give 2,4-bis-benzyloxy-5-bromo-benzoic acid benzyl ester as a white solid (47.8 g, 95%). M.p.: 74-76° C.; 400 MHz 1H NMR (CDCl3) δ: 8.13 (s, 1H), 7.41-7.28 (m, 15H), 6.53 (s, 1H), 5.32 (s, 2H); 5.12 (s, 2H), 5.08 (s, 2H); LCMS: 503, 505 [M+H].

Provenance & Evidence