Iodine → 1-(p-Chlorophenyl)-1-[2-fluoro-3-(m-phenoxyphenyl)propenyl]cyclopropane

Participants

Reaction Steps

A Grignard reagent, prepared from 3-phenoxyphenyl bromide (0.33 g) in dry tetrahydrofuran (2 ml) and magnesium (30 mg) under nitrogen using iodine as an initiator at ca 40 C for 50 min, was cooled to room temperature then treated with cuprous bromide (ca 20 mg) for 10 min. After cooling to -78° C., a solution of 1-(3-acetoxy-2-fluoroprop-1-enyl)-1-(4-chlorophenyl)cyclopropane (Example 17) (0.32 g) in tetrahydrofuran was added slowly with stirring, then the mixture was allowed to warm to room temperature overnight. The mixture was treated with water (4 ml), then extracted with diethyl ether (3×20 ml). The combined organic extracts were washed with water (2×10 ml), dried, and evaporated under reduced pressure. The residue was purified by preparative thin layer chromatography (solvent: diethyl ether/hexane; 1:9) and then preparative high performance liquid chromatography (column: C18; solvent: methanol; flow rate: 8 ml/min) to afford 1-(4-chlorophenyl)-1-(2-fluoro-3-(3-phenoxyphenyl)prop-1-enyl)cyclopropane (98 mg, 22%).

Provenance & Evidence