Ethyl Acetate → Methyl 4-[4-(trifluoromethoxy)benzyl]benzoate

Participants

Reaction Conditions

Reaction Steps

A solution of methyl 4-(bromomethyl)benzoate (93) (0.23 mL, 1.0 mmol) and 4-(trifluoromethoxy)phenylboronic acid (44) (0.24 g, 1.1 mmol) in DME (3 mL) and 2M aqueous K2CO3 (1 mL) was degassed, then treated with tetrakis(triphenylphosphine) palladium (58 mg, 50 μmol). The reaction mixture was stirred under N2 at 105° C. for 24 h, and then EtOAc (250 mL) was added. The organic layer was washed with water, the aqueous layer was re-extracted with EtOAc (100 mL), and the combined organic layers were washed with brine, dried (Na2SO4) and concentrated under reduced pressure. The residue was chromatographed on silica gel, eluting with petroleum ether/EtOAc (9:1), to give methyl 4-[4-(trifluoromethoxy)benzyl]benzoate (94) (215 mg, 68%) as a colourless oil; 1H NMR (CDCl3) δ 7.98-7.94 (m, 2H), 7.26-7.22 (m, 2H), 7.20-7.12 (m, 4H), 4.03 (s, 2H), 3.90 (s, 3H); HREIMS calcd for C16H13F3O3 m/z (TO 310.0817, found 310.0815.

Provenance & Evidence