[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:11]([F:14])([F:13])[F:12])=[C:6]([CH:10]=1)[C:7](O)=[O:8].O.C(=O)([O-])[O-].[K+].[K+]>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:11]([F:12])([F:13])[F:14])=[C:6]([CH2:7][OH:8])[CH:10]=1Add borane-THF complex (3.34 mL, 3.34 mmol) slowly to an ice-methanol cooled bath solution of 5-chloro-2-trifluoromethyl-benzoic acid (500 mg, 2.23 mmol) in THF (2 mL). Stir overnight at room temperature. Add water (1 mL) and solid potassium carbonate. Filter and concentrate to give an oil residue. Chromatograph on silica gel, eluting with 10:90 to 1:1 ethyl acetate:hexanes to give (5-chloro-2-trifluoromethylphenyl)-methanol as a white solid (347 mg, 75%). 1H NMR (400 MHz, MeOH-d4) δ 7.84 (s, 1H), 7.68 (d, 1H, J=8.4 Hz), 7.48 (d, 1H, J=8.4 Hz), 4.81 (s, 2H).
Wird geladen…
