Water → Methyl 1-(5-bromopyridin-3-yl)cyclopropanecarboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 2-(5-bromopyridin-3-yl)acetate (4 g, 17.4 mmol) in DMF (80 mL), cooled at 0° C. with an ice bath, was added 60% NaH in mineral oil (0.918 g, 38.3 mmol) and the reaction mixture was stirred at 0° C. for 15 min. Then, a solution of 1,2-dibromoethane (3.27 g, 17.4 mmol) in DMF (16 mL) was added at 0° C. After the addition, the mixture was stirred at room temperature for 1 h. Two other portions of 60% NaH in mineral oil (2×0.2 g) were added sequentially, until conversion was complete. Then, the reaction mixture was poured into H2O (50 mL) and extracted with EtOAc (3×125 mL). The organic layers were combined, dried over Na2SO4, filtered and evaporated to dryness to give the title compound (4.764 g, 99%) as a brown oil, which was used with no further purification. MS: 256.0 and 258.0 (M+H+).

Provenance & Evidence