Methanol → Methyl 4-bromobenzoate

Participants

Reaction Steps

4-bromobenzoic acid (1.10 g, 5.39 mmol) was dissolved in MeOH (30 mL). Concentrated H2SO4 (140 mL) was added and the reaction was allowed to reflux for a total of 29 hr. The reaction was quenched with dilute Na2CO3 (15 mL) and equal volume of EtOAc. The solution was diluted with brine to promote phase separation. The aqueous layer was extracted a second time with EtoAc. The combined organic layers were dried over anhydrous Na2SO4 and evaporated to dryness to afford 4-bromobenzoic acid methyl ester (1.124 g, 5.22 mmol, 97%). 1H-NMR (CD2Cl2, 500 MHz) δ (ppm): 3.89 (s, 3H); 7.56 (d, J=16.8 Hz, 2H); 7.88 (d, J=16.8 Hz, 2H).

Provenance & Evidence