Methanol → (4-Iodo-2-(trifluoromethyl)phenyl)methanol

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-iodo-2-(trifluoromethyl)benzoic acid (for a preparation see Intermediate 31)(16.7 g, 52.8 mmol) in THF (150 ml) at ambient temperature under nitrogen was added 1.0 M borane-tetrahydrofuran complex (100 ml, 100 mmol, Aldrich) dropwise. The solution was heated to 80° C. for 1.5 h. To the solution at ambient temperature was added methanol (75 ml) and then heated to 80° C. for 1 h. The solvent was removed in vacuo to leave a mobile oil. The residue was partitioned between ethyl acetate (200 ml) and 2 N aqueous HCl (100 ml). The phases were separated and the organic phase washed with 2 N aqueous sodium hydroxide (100 ml), brine (50 ml), then dried (MgSO4), filtered and the solvent removed in vacuo to give [4-iodo-2-(trifluoromethyl)phenyl]methanol as a pale brown solid (14.8 g).

Provenance & Evidence