Chloroiodomethane → 1-(Cyclopropyloxy)-2-iodo-4-(trifluoromethoxy)benzene

Participants

Reaction Conditions

Reaction Steps

1-(Vinyloxy)-2-iodo-4-(trifluoromethoxy)benzene (Description 11; 7.6 g, 23 mmol) and chloroiodomethane (5.4 mL, 74 mmol) were dissolved in 1,2-dichloroethane (40 mL) and cooled to 0° C. Diethyl zinc (3.8 mL, 36.8 mmol) was then added dropwise. The solution was allowed to warm to room temperature for 10 minutes, then cooled back to 0° C. when it was quenched with saturated aqueous ammonium chloride solution (50 mL). The suspension formed was extracted with 50% diethyl ether/hexane (2×100 mL) and the extracts dried (MgSO4). Concentration yielded a yellow oil which was purified by silica chromatography to give the title compound as a clear oil (5.84 g, 17 mmol).

Provenance & Evidence