Reaction SMILES: CC(C)([O-])C.[K+].[Br-].[F:8][C:9]1[CH:10]=[C:11]([CH:32]=[C:33]([F:43])[C:34]=1[O:35][Si:36]([C:39]([CH3:42])([CH3:41])[CH3:40])([CH3:38])[CH3:37])[CH2:12][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[CH2:44]([Si:47]1([C:61]2[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=2)[CH2:52][CH2:51][CH:50]([CH:53]2[CH2:58][CH2:57][CH:56]([CH:59]=O)[CH2:55][CH2:54]2)[CH2:49][CH2:48]1)[CH2:45][CH3:46].O>C1COCC1>[F:43][C:33]1[CH:32]=[C:11]([CH:12]=[CH:59][CH:56]2[CH2:55][CH2:54][CH:53]([CH:50]3[CH2:49][CH2:48][Si:47]([CH2:44][CH2:45][CH3:46])([C:61]4[CH:62]=[CH:63][CH:64]=[CH:65][CH:66]=4)[CH2:52][CH2:51]3)[CH2:58][CH2:57]2)[CH:10]=[C:9]([F:8])[C:34]=1[O:35][Si:36]([C:39]([CH3:40])([CH3:41])[CH3:42])([CH3:37])[CH3:38]
Reactant: CC(C)(C)[Si](C)(C)Oc1c(F)cc(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)cc1F
Reactant: CCC[Si]1(c2ccccc2)CCC(C2CCC(C=O)CC2)CC1
Agent: CC(C)(C)[O-]
Agent: [Br-]
Agent: [K+]
Solvent: C1CCOC1
Solvent: O
Product: CCC[Si]1(c2ccccc2)CCC(C2CCC(C=Cc3cc(F)c(O[Si](C)(C)C(C)(C)C)c(F)c3)CC2)CC1
Temperature: 25 °C
Reaction time: 2 h

Procedure:
12.0 g of potassium t-butoxide was added to a mixture of 62 g of 3,5-difluoro-4-(t-butyldimethylsiloxy)benzyltriphenylphosphonium bromide and 200 ml of THF to obtain an orange-colored ylide solution. A mixture of 35.0 g of 4-(4-n-propyl-4-phenyl-4-silacyclohexyl)cyclohexane carbaldehyde in 50 ml of THF was added to the above solution. The mixture was agitated at room temperature for 2 hours, after which it was poured into iced water, followed by extraction with ethyl acetate. The ethyl acetate solution was washed, dried and concentrated by a usual manner. The resultant residue was added to n-hexane and the resultant triphenylphosphine oxide crystals were removed by filtration. The resultant filtrate was concentrated. The residue was purified through silica gel chromatography to obtain 4-(4-(2-(3,5-difluoro-4-(t-butyldimethylsiloxy)phenyl)ethenyl)cyclohexyl)-1-propyl-1-phenyl-1-silacyclohexane. This compound was dissolved in 200 ml of ethyl acetate and hydrogenated in the presence of 200 mg of a platinum oxide catalyst at a hydrogen pressure of 0.1 MPa. After consumption of the theoretical amount of hydrogen, the catalyst was removed by filtration. The resultant filtrate was concentrated. 100 ml of a THF solution of 1 mol/liter of tetrabutylammonium fluoride was added to the concentrate, followed by agitation at room temperature for 3 hours. The reaction mixture was poured into 10% hydrochloric acid, followed by ordinary washing, drying and concentration. The resultant residue was purified through silica gel chromatography. The purified compound was reacted with 24 g of sodium hydride in 12,3-dimethyl-2-imidazolidinone, to which 15 g of 1-bromo-2,2-difluoroethane was added, followed by agitation at 50° C. for 12 hours. The resultant mixture was washed with brine, dried and concentrated by a usual manner. A methylene chloride solution of 1 mol/liter of iodine monochloride was added to the resultant residue and agitated for 1 hour. Thereafter, 10 ml of methanol and 30 ml of triethylamine were added to the solution. After agitation for 1 hour, the mixture was washed, dried and concentrated by a usual manner. The resultant residue was dissolved in 100 ml of THF, to which a solution of 10.0 g of aluminium lithium hydride in 100 ml of THF was added. The reaction mixture was refluxed under agitation for 1 hour. Subsequently, the mixture was poured into 200 ml of 5% hydrochloric acid and extracted with ethyl acetate. After washing, drying and concentration by a usual manner, the extract was purified through silica gel chromatography and then recrystallized to obtain 15.6 g of an intended trans isomer.