Benzyl Bromide → Benzyl 2-hydroxy-4-(trifluoromethyl)benzoate

Participants

Reaction Steps

BnBr (1.20 mL, 8.325 mmol) was added to a solution of 2-hydroxy-4-(trifluoromethyl)benzoic acid (1.50 g, 7.277 mmol) in TBAF (10 mL, 1 M solution in THF) and the mixture was stirred at r.t. for 2 h. The reaction mixture was poured into NaHCO3 (saturated aqueous solution, 100 mL) and extracted with EtOAc (100 mL). It was dried over Na2SO4 (anhydrous), filtered and concentrated. The crude residue was flash chromatographed on SiO2 (5→30% EtOAc/hexanes) to furnish 2.18 g of benzyl 2-hydroxy-4-(trifluoromethyl)benzoate (colourless oil, yield: quantitative).

Provenance & Evidence