Water → 1-(4-Bromophenyl)-3,3-dimethoxycyclobutanecarbonitrile

Participants

Reaction Conditions

Reaction Steps

A suspension of sodium hydride (2 g, 50.0 mmol) in DMF (20 ml) was cooled to 0 degree before 2-(4-bromophenyl)acetonitrile (4 g, 20.40 mmol) was added slowly, The suspension was stirred at 0 degree for another 10 min before 1,3-dibromo-2,2-dimethoxypropane (2.62 g, 10.00 mmol) was added. The reaction mixture was stirred at 60° C. for 20 h before cooled to room temperature, poured into water (75 ml) and extracted with ethyl acetate (2×50 ml). The combined organic phase was washed with water (75 ml), brine (50 ml) and concentrated. The crude product was purified by column (100 g, biotage) eluted with ethyl acetate/cyclohexane (0-10%) to afford product 1.7 g (59% yield). 1H NMR (500 MHz, DMSO-d6): 7.46 (d, 2H), 7.29 (d, 2H), 3.21 (s, 3H), 3.11 (s, 3H), 3.03 (d, 2H), 2.62 (d, 2H).

Provenance & Evidence