Chloroiodomethane → HCID 86703560, compound

Participants

Reaction Conditions

Reaction Steps

To a cooled (0° C.) solution of tert-butyl 5-cyclopropyl-2-fluoro-4-((1-methyl-4-methylenecyclohexyl)methoxy)benzoate (0.30 g, 0.804 mmol) in 1,2-dichloroethane (2 mL), was added chloroiodomethane (0.21 mL, 2.65 mmol), followed by diethylzinc (1M solution in hexanes, 1.33 mL, 1.33 mmol). The reaction mixture was stirred at 0° C. for 2 hours and then quenched with 1N aqueous hydrochloric acid solution. The aqueous layer was separated and extracted with dichloromethane (3×30 mL). The combined organics were dried over anhydrous sodium sulfate and concentrated in vacuo. Purification of the residue by column chromatography (0% to 5% ethyl acetate in hexanes) afforded the title compound (0.29 g, 93%) as a colorless oil: MS (ES+) m/z 333.2 (M−55).

Provenance & Evidence