Benzyl Alcohol → Benzyl 4-bromo-2-methylbenzoate

Participants

Reaction Steps

To a suspension of 1.26 g (5.86 mmol) of 4-bromo-2-methylbenzoic acid in 10 mL of CH2Cl2 was added 1.5 mL (17.6 mmol) of oxalyl chloride and two drops of DMF. After stirring at rt overnight, the reaction mixture was concentrated. The residue was dried azeotropically using toluene (3×5 mL) and then dissolved in 10 mL of CH2Cl2, to which 667 μL (6.45 mmol) of benzyl alcohol, 1.23 mL (8.79 mmol) of triethylamine, and catalytic amount of 4-dimethylaminopyridine were added. After stirring at rt for 1 h, the reaction mixture was poured into 20 mL brine. The aqueous layer was extracted with CH2Cl2 (3×10 mL). Organic layers were combined, dried over MgSO4, and concentrated. Chromatography on Biotage 40S cartridge using 1:19 v/v EtOAc/hexanes as the eluant afforded 1.58 g of the title compound: 1H NMR (500 MHz, CDCl3) δ 2.58 (s, 3H), 5.33 (s, 2H), 7.33-7.44 (m, 7H), 7.81 (d, J=8.5, 1H).

Provenance & Evidence