Ethyl Acetate → Methyl 3-((di-tert-butoxyphosphoryloxy)methyl)benzoate

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of methyl-3-(bromomethyl)benzoate (0.5 g, 2 mmol) in THF (10 mL) was added potassium ditertiary butyl phosphate (0.5 g, 2 mmol). The reaction flask was heated to 70° C. for 2 h. After the flask was cooled to rt, EtOAc (50 mL) was added to the mixture. The organics were washed with brine (2×10 mL), dried over anhydrous sodium sulfate, and evaporated under vacuum to yield methyl 3-((di-tert-butoxyphosphoryloxy)methyl)benzoate (0.35 g, 0.9 mmol). 1H NMR (400 MHz, CHCl3-d): δ 1.47 (s, 18H), 3.91 (s, 3H), 5.03 (d, 2H, J=7.6 Hz), 7.44 (t, J=7.6 1H), 7.60 (dd, J=1.2 and 7.2), 7.98 (ddd, J=1.2, 2.8 and 7.6, 1H), 8.05 (t, J=0.4, 1H).

Provenance & Evidence