Chloroiodomethane → HCID 131735156, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of diethylzinc (1M in hexane, 2.0 mL, 2.0 mmol) in dichloromethane (3.7 mL) at −4° C. was added chloroiodomethane (714 mg, 4.0 mmol) dissolved in dichloromethane (1 mL) dropwise. The reaction mixture was stirred at 0° C. for 15 minutes. A solution 2-bromo-6-(1-((tert-butyldimethylsilyl)oxy)vinyl)pyridine (200 mg, 0.6 mmol) in dichloromethane (3.0 mL) was added. The reaction mixture was stirred at 0° C. for 2 h. A cold saturated aqueous solution of ammonium chloride was added and the mixture was extracted with dichloromethane. The organics were dried over sodium sulfate and concentrated under reduced pressure. The crude material was purified via flash chromatography (100% heptanes) to afford 2-bromo-6-(1-((tert-butyldimethylsilyl)oxy)cyclopropyl)pyridine (120 mg, 58%). 1H NMR (400 MHz, CDCl3) δ 0.11 (s, 6H), 0.95 (s, 9H), 1.22-1.28 (m, 2H), 1.39-1.45 (m, 2H), 7.23 (dd, 1H), 7.47 (t, 1H), 7.60 (dd, 1H).

Provenance & Evidence