Hydrochloric Acid → 3-Amino-3-(4-phenoxyphenyl)acrylonitrile

Participants

Reaction Conditions

Reaction Steps

A 2.5 M THF solution of n-BuLi (20.49 mL, 51.2 mmol) was added to a solution of diisopropylamine (7.30 mL, 51.2 mmol) in THF (165 mL) at −78° C. The mixture was stirred at 0° C. for 20 min and cooled to −78° C. Acetonitrile (2.68 mL, 51.2 mmol) was added to give a white cloudy solution. After 30 min at −78° C., a solution of 4-phenoxybenzonitrile (10 g, 51.2 mmol) in THF (35 mL) was added. After 1.5 h at −78° C., saturated ammonium chloride (50 mL), water (25 mL) and 1 N HCl (25 mL) were added. The THF was evaporated in vacuo. The residue was extracted with ethyl acetate (200 mL). The ethyl acetate phase was washed with 0.1 N HCl (50 mL) and brine (10 mL), dried (MgSO4) and concentrated. The resulting mixture was triturated with a mixture of dichloromethane and hexanes. Filtration of the suspension gave 3-amino-3-(4-phenoxyphenyl)acrylonitrile as white solid (7.364 g). The filtrate was concentrated to a small volume and filtered to give additional product (2.501 g). The total amount of the product was 9.865 g (82% yield). 1H NMR (400 MHz, CDCl3) δ ppm 7.44-7.50 (2H, m), 7.39 (2H, t, J=7.91 Hz), 7.18 (1H, t, J=7.40 Hz), 6.98-7.08 (4H, m), 4.88 (2H, br. s), 4.22 (1H, s); MS (ES+) m/z: 237 (M+H).

Provenance & Evidence