Sodium Hydroxide → 2-Amino-1-(3,4-difluorophenyl)ethan-1-ol

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Reaction Steps

To a solution consisting of 3,4-difluorobenzaldehyde (3.85 g, 27.1 mmol), zinc iodide (104.9 mg, 0.329 mmol) and THF (5 mL) at 0° C. under nitrogen was added TMSCN (4.60 mL, 33.9 mmol). The resultant mixture was stirred for 3.5 h at 0° C. and then cannulated into a 0° C. suspension of LiAlH4 (1.41 g, 67.7 mmol) in THF (80 mL). The resultant mixture was allowed to gradually warm to rt with stirring for 21 h. The reaction mixture was then re-cooled to 0° C. and carefully treated with water (2.57 mL) followed by 15% aq. NaOH (2.57 mL) and lastly with water (7.7 mL). The resultant mixture was stirred for 1 h, the solids removed by vacuum filtration and the filtrate concentrated. The resulting crude product was purified by FCC(CH2Cl2/MeOH/NH3) to give the desired product.

Provenance & Evidence