5-Chloro-2-iodobenzoic acid → (5-Chloro-2-iodophenyl)methanol

Participants

Reaction Steps

Borane-dimethylsulfide complex (3.7 mL, 38.9 mmol) was added slowly to a cold (0° C.) solution of 5-chloro-2-iodo-benzoic acid (10 g, 35.4 mmol) in THF (20 mL). The reaction mixture was allowed to warm to rt, stirred for 8 h, quenched by addition of a saturated aqueous solution of ammonium chloride, and extracted with EtOAc. The organic layer was dried (Na2SO4), filtered, and concentrated to provide 9.5 g of the title compound. tR: 4.72 min (HPLC 2); Rf=0.66 (hexane/EtOAc, 7:3).

Provenance & Evidence