Water → 1-(Chloromethyl)cycloheptane-1-carbonitrile

참여 물질

반응 단계

A solution of cycloheptanecarbonitrile (12.3 g), 100 mmol) in THF (50 ml) was added dropwise to a well stirred solution of lithium diisopropylamide (105 mmol) in THF/hexane (75 ml/60 ml) under nitrogen, keeping the temperature at -65°. After 1 h, the solution was allowed to warm to ambient temperature and added dropwise to a well stirred solution of bromochloromethane (32.5 ml; 500 mmol) in THF (50 ml) under nitrogen keeping the temperature between -50° and -60°. After 10 min, the solution was allowed to warm to ambient temperature, poured into water (250 ml) and the aqueous mixture extracted with chloroform (3×150 ml). The extracts were washed with 2N-HCl (2×50 ml), saturated aq. NaHCO3 (100 ml), and water (100 ml), then dried (MgSO4) and evaporated under reduced pressure to give a brown oil (18.0 g). Distillation gave the title compound (12.65 g), b.p. 78°-80° at 0.25 mmHg.

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