3-Hydroxybenzoic Acid → 4-Bromo-3-hydroxybenzoic acid

Participants

Reaction Steps

The title compound was prepared according to the method reported by Buehler et al.[Buehler, 1946] using 3-hydroxybenzoic acid (18.2 g, 132.0 mmol) and Br2 (6.76 mL, 132.0 mmol) in glacial AcOH (250 mL) to give 4-bromo-3-hydroxybenzoic acid as a colourless crystalline solid (3.43 g, 12%) after recrystallisation from Et2O/n-hexane; mp. 225-226° C. (lit.[Beyer, 1921] 227-228° C.); δH (270 MHz, DMSO-d6) 7.28 (dd, J=8.2, 2.0, 1H), 7.51 (d, J=1.7, 1H), 7.60 (d, J=10.66 (bs, 1H,—exchanges with D2O, ArOH) and 13.04 (bs, 1H—exchanges with D2O, ArCOOH); LRMS (FAB+) m/z (rel. intensity) 218 (94, [C7H581BrO3+H]), 216 (100, [C7H579BrO3+H]); LC-MS (APCI−): tR=1.38 min, m/z 216.78 (M−H); HPLC: tR=1.35 min (100%); HRMS Found 218.94656; C7H681BrO3 requires 218.94798.

Provenance & Evidence