Water → [5-Chloro-2-(trifluoromethyl)phenyl]methanol

HRID 252087Notes

Reaction equation

HRID 252087 reaction equation
[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]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 27738595-Chloro-2-(trifluoromethyl)benzoic acid

Product 1

HCID 2778112[5-Chloro-2-(trifluoromethyl)phenyl]methanolYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add 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).

Workup

  1. filtrationFilter
  2. concentrationconcentrate
  3. customto give an oil residue
  4. washChromatograph on silica gel, eluting with 10:90 to 1:1 ethyl acetate

Sources & evidence

ORD record
ord-98e6c6792b9d49b4bcfae59b6805bac2
Source dataset
uspto-grants-2011_01
Patent number
US07868014B2

Reaction notes

Loading…