[F:1]/[C:2](/[CH:5]1[CH2:10][CH2:9][CH:8]([CH2:11][CH2:12][CH3:13])[CH2:7][CH2:6]1)=[CH:3]/[F:4].[Li]C(C)(C)C.[I:19]I.O>C1COCC1>[F:1]/[C:2](/[CH:5]1[CH2:10][CH2:9][CH:8]([CH2:11][CH2:12][CH3:13])[CH2:7][CH2:6]1)=[C:3](/[F:4])\[I:19]7.0 g (26.3 mmol) of 1-((E)-1,2-difluorovinyl)-4-propylcyclohexane are initially introduced in 150 ml of THF at −55° C., and 20.5 ml (30.2 mmol, 15% soln. in n-pentane) of t-BuLi are metered in. After 2 h at this temperature, a solution of 7.67 g (30.0 mmol) of iodine in 50 ml of THF is added dropwise. The mixture is slowly warmed to 0° C., and water is added. The batch is extracted with MTBE, and the organic phase is washed with water and saturated sodium chloride solution. The solution is dried using sodium sulfate and concentrated to dryness. The residue is purified by column chromatography (SiO2, pentane), giving 1-((Z)-1,2-difluoro-2-iodovinyl)-4-propylcyclohexane as a pale-violet oil.
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