(Chloromethyl)pentafluorobenzene → (+/-) trans-2,2-Dimethyl-3-dichlorovinyl-cyclopropanecarboxylic acid pentafluorobenzyl ester
Reaction equation
[CH3:1][C:2]1([CH3:12])[C@@H:4]([CH:5]=[C:6]([Cl:8])[Cl:7])[C@@H:3]1[C:9]([O-:11])=[O:10].[K+].[F:14][C:15]1[C:20]([CH2:21]Cl)=[C:19]([F:23])[C:18]([F:24])=[C:17]([F:25])[C:16]=1[F:26]>C(#N)C>[F:14][C:15]1[C:20]([CH2:21][O:10][C:9]([C@H:3]2[C@H:4]([CH:5]=[C:6]([Cl:8])[Cl:7])[C:2]2([CH3:12])[CH3:1])=[O:11])=[C:19]([F:23])[C:18]([F:24])=[C:17]([F:25])[C:16]=1[F:26]Participants
4
Procedure
0.1 mole of potassium (±) trans-2,2-dimethyl-3-dichlorovinyl-cyclopropanecarboxylate and 0.1 mole of pentafluorobenzyl chloride were heated in acetonitrile until the reaction was complete. After concentrating, taking up in water/petroleum ether and concentrating the organic phase, a colorless oil was obtained, in the NMR spectrum of which the doublet mentioned in Example 2 for the vinyl proton of the cis-ester was lacking.