Dimethyl Sulfide → (5-Bromo-2-iodophenyl)methanol

Participants

Reaction Conditions

Reaction Steps

To a stirred mixture of acid 2-iodo-5-bromobenzoic acid (15.0 g, 45.9 mmol) in dry THF (100 mL) under argon was added neat BH3.DMS (16.0 mL, 169 mmol) dropwise over 20 minutes. The resulting mixture was heated at 65° C. for 8 hours, cooled to room temperature and quenched by the dropwise addition of water (40 mL). The reaction mixture was concentrated in vacuo. The crude alcohol was diluted with of EtOAc (300 mL), washed with 1N NaOH (2×30 mL), 1N HCl (1×30 mL), saturated aqueous NaHCO3 solution (1×30 mL) and brine (1×30 mL). The EtOAc layer was dried (MgSO4), filtered and concentrated in vacuo to give 2-iodo-5-bromobenzyl alcohol (13.8 g, 96%). 1H NMR (CDCl3): δ 7.56 (d, 1H, J=8.25 Hz), 7.54 (s, 1H), 7.04 (d, 1H, J=8.25 Hz), 4.47 (s, 2H). HPLC: Rt=3.12 min. m/z=312 (M+H+).

Provenance & Evidence