[F:1][C:2]([F:18])([F:17])[C:3]1[CH:8]=[CH:7][C:6]([O:9][C:10]([CH2:15][F:16])([C:13]#[CH:14])[CH2:11][F:12])=[CH:5][CH:4]=1.COC(C)(C)C.CC(C)([O-])C.[K+].[Br:31]Br>CCCCCC.C(O)(C)(C)C>[F:1][C:2]([F:17])([F:18])[C:3]1[CH:8]=[CH:7][C:6]([O:9][C:10]([CH2:11][F:12])([C:13]#[C:14][Br:31])[CH2:15][F:16])=[CH:5][CH:4]=1
An amount (13.9 g) of 1-fluoro-2-fluoromethyl-3-butyn-2-yl 4-trifluoromethylphenyl ether was dissolved in a solvent consisting of a mixture of tert-butyl methyl ether (100 ml) and tert-butyl alcohol (150 ml). To the solution under cooling with ice, potassium tert-butoxide (7.1 g) was added under a nitrogen atmosphere; after stirring for a while, bromine (3 ml) was added dropwise. After the end of the dropwise addition, the mixture was stirred for 30 minutes under stirring with ice. Hexane was added to the reaction mixture, which was then washed with water and a saturated aqueous solution of sodium chloride. The mixture was dried with anhydrous sodium sulfate and concentrated under reduced pressure to give the titled compound (18.1 g).
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