Dabco → HCID 86737383, compound

Participants

Reaction Steps

This compound was prepared in the manner of Examples 8, 9, and 10 using 2.3 g (0.009 mole) of cis, trans-3-(2,3-dichloro-3,3-difluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxylic acid (compound 4.4, Table III), 0.6 g (0.009 mole) of potassium hydroxide, 2.8 g (0.009 mole) of 3-bromomethyl-2,4-dichloro[1,1'-biphenyl] and 0.1 g of 1,4-diazabicyclo[2.2.2]octane in 50 ml of heptane and 50 ml of acetonitrile. The crude product was purified by removing the volatiles by distillation using a Kugelrohr bulb to bulb distilling system at 130°-140° C./0.3-0.5 mm. The pot residue was subjected to column chromatography on silica gel, eluting with hexane, then 25:1-hexane:ethyl acetate. Appropriate fractions were combined and subjected to liquid chromatography using 66.6:1-hexane:ethyl acetate as the eluant. The appropriate fractions were combined to give 0.29 g of (2,4-dichloro[1,1'-biphenyl]-3-yl)methyl cis-3-(2,3-dichloro-3,3-difluoro- 1-propenyl)-2,2-dimethylcyclopropanecarboxylate. The nmr and ir spectra were consistent with the proposed structure.

Provenance & Evidence