Methanol → Methyl 4-Bromo-3-hydroxybenzoate

Participants

Reaction Steps

The title compound was prepared according to the method reported by Faltis et al.[Faltis, 1941] using 4-bromo-3-hydroxybenzoic acid (5.7 g, 26.26 mmol) and concentrated sulphuric acid (98% solution, 1.4 mL, 26.26 mmol) in anhydrous MeOH (150 mL) to give methyl 4-bromo-3-hydroxybenzoate as a colourless crystalline powder (5.4 g, 89%) after recrystallisation from MeOH; mp. 126-127° C., lit.[Faltis, 1941] (hexane) 124-125° C.; δH (270 MHz, CDCl3) 3.90 (s, 3H), 5.75 (bs, 1H—exchanges with D2O), 7.46 (dd, J=8.4, 2.0, 1H), 7.53 (d, J=8.2, 1H), 7.67 (d, J=1.7, 1H); LRMS (FAB+) m/z (rel. intensity) 232.0 (94, [C8H781BrO3+H]), 230.8 (100, [C8H779BrO3+H]); LC-MS (APCI−): tR=3.72 min, m/z 230.96 (M−H); HPLC: tR=2.04 min (99%); HRMS (FAB+) Found 232.96325; C8H8O381Br requires 232.96363.

Provenance & Evidence