4'-Trifluoromethyl-biphenyl-3-carboxylic acid → 4'-(Trifluoromethyl)[1,1'-biphenyl]-3-methanol

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Reaction Steps

The carboxylic acid 2.1 (13.3 g, 50 mmol) in anhydrous THF (100 mL) was added dropwise to LiAlH4 (2.9 g, 75 mmol) in anhydrous THF (150 mL) at 0° C. over 30 minutes. The resulting mixture was slowly warmed to room temperature and stirred for 4 hours. The reaction was slowly quenched with water (2.9 mL) at 0° C., 15% NaOH aqueous solution (2.9 mL) and another portion of water (8.7 mL). The mixture was dried over Na2SO4 and concentrated to give a white solid (11.9 g). The crude product (2.2) was used in the next step without further purification.

Provenance & Evidence