Hydrochloric Acid → Methyl 2-bromo-5-methoxybenzoate

Participants

Reaction Steps

To a stirred solution of 2-bromo-5-methoxybenzoic acid (Aldrich 384003; 5.0 g, 21.6 mmol) in methanol (80 mL) was added concentrated hydrochloric acid (2 mL) and the mixture was heated under reflux for 18 hours. The resulting solution was cooled, the solvent was removed in vacuo, water (100 mL) was added and the mixture was extracted with ethyl acetate (2×100 mL). The combined extracts were washed with saturated aqueous sodium hydrogen carbonate, dried over MgSO4, filtered and evaporated to obtain methyl 2-bromo-5-methoxybenzoate as a light brown oil (4.50 g, 85%); NMR Spectrum δH (300 MHz, CDCl3) 7.53 (1H, d, J 8.8 Hz, 3-H), 7.32 (1H, d, J 3.0 Hz, 6-H), 6.89 (1H, dd, J 3.0, 8.8 Hz, 4-H), 3.94 (3H, s, Ar OCH3) and 3.82 (3H, s, CO2CH3) (data in accordance with published values, see Barhate, N. B.; Gajare, A. S.; Wakharkar, R. D.; Bedekar, A. V. Tetrahedron 1999, 55, 11127-11142); νmax/cm−1 (thin film) 2951, 1732 (C═O), 1592, 1472, 1433, 1289, 1250, 1227, 1099, 1017, 975, 823, 792 (data in accordance with published values, see Barhate, N. B.; Gajare, A. S.; Wakharkar, R. D.; Bedekar, A. V. Tetrahedron 1999, 55, 11127-11142); Rf (hexane-ethyl acetate 5:1) 0.58.

Provenance & Evidence