3-Methyl-2-butanone → 2-(4-Iodophenyl)-3-methylbutan-2-ol

Participants

Reaction Conditions

Reaction Steps

n-Butyl lithium (139 mL of a 2M solution in hexanes, 277 mmol) was added via canula to a stirred solution 1,4-diiodobenzene (89.0 g, 277 mmol) in THF (500 mL) at −78° C. such that the internal temperature was maintained below −65° C. during the addition process. After 0.5 h, 3-methyl-2 butanone (24.0 g, 280 mmole) was added via syringe, again maintaining the internal temperature below −65° C. After 0.5 h, the reaction mixture was warmed to 0° C. and quenched with saturated aqueous ammonium chloride. The resulting mixture was dried (MgSO4), concentrated in vacuo, and the crude residue purified by flash chromatography on silica gel (gradient elution; 10-25% EtOAc/hexanes) to afford the title compound 5a. 1H NMR (500 MHz, CDCl3) δ 7.67 (d, 2H, J=7.5 Hz), 7.20 (d, 2H, J=7.5 Hz), 3.79 (s, 1H), 2.00 (m, 1H, J=7.0 Hz), 1.52 (s, 3H), 0.92 (d, 3H, J=7.0 Hz), 0.81 (d, 3H, J=7.0 Hz).

Provenance & Evidence