Aluminium lithium hydride → 2-(4-Aminomethyl-3-fluoro-phenyl)-propan-2-ol

Participants

Reaction Steps

To a stirred solution of 2-fluoro-4-(1-hydroxy-1-methyl-ethyl)-benzonitrile (1.95 g, 11.0 mmol) in tetrahydrofuran (30 mL) at 0° C. was added drop-wise a 1.0 M solution of lithium aluminium hydride in tetrahydrofuran (34 mL, 34.0 mmol). The reaction mixture was warmed to ambient temperature then refluxed for 30 minutes. The reaction mixture was cooled to 0° C., then quenched with methanol (20 mL) added drop-wise. The reaction mixture was then diluted with chloroform (700 mL) and washed with water (100 mL). The resulting suspension was filtered through Celite, after which the organic extract contained in the filtrate was separated, dried over magnesium sulfate (MgSO4), and concentrated to give 1.6 g 2-(4-aminomethyl-3-fluoro-phenyl)-propan-2-ol as an amber gum.

Provenance & Evidence