Methanol → (5-Chloro-2-iodophenyl)methanol

Participants

Reaction Conditions

Reaction Steps

Borane methylsulfide (7.3 mL, 73 mmol) was added to a stirred solution of 5-chloro-2-iodobenzoic acid (17.17 g, 60.79 mmol) in THF (40 mL) and trimethylborate (20 mL), maintaining the internal temperature at 20-25° C. After 16 h methanol (8.87 mL, 0.219 mol) was added cautiously and the solution was evaporated in vacuo, azeotroping with methanol (3×50 mL). The resulting solid was recrystallized (hexanes/ethyl acetate, 5:1, 120 mL) to give 5-chloro-2-iodobenzyl alcohol (12.2 g): 1H NMR (CDCl3, 400 MHz) δ 2.00 (br s, 1H), 4.64 (s, 2H), 7.00 (dd, J=2.6, 8.4 Hz, 1H), 7.49 (d, J=2.4, 1H), 7.72 (d, J=8.2 Hz, 1H).

Provenance & Evidence