[Br:1][C:2]1[CH:3]=[C:4]([CH:8]([C:10]2[S:11][C:12]([CH2:15][CH3:16])=[CH:13][CH:14]=2)O)[CH:5]=[CH:6][CH:7]=1.C([SiH](CC)CC)C.C(=O)([O-])O.[Na+]>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][C:10]2[S:11][C:12]([CH2:15][CH3:16])=[CH:13][CH:14]=2)[CH:5]=[CH:6][CH:7]=1The above 3-bromophenyl-5-ethyl-2-thienylmethanol (2.90 g) was dissolved in dichloromethane (38 ml), and the mixture was cooled to −78° C. under argon atmosphere. To the mixture were added triethylsilane (6.18 ml) and boron trifluoride diethyl ether complex (2.45 ml), and the mixture was gradually warmed to room temperature over a period of one hour. The mixture was basified with a saturated aqueous sodium hydrogen carbonate solution, and the dichloromethane layer was collected, dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane) to give the desired 3-bromo-(5-ethyl-2-thienylmethyl)benzene (2.57 g) as a colorless syrup. APCI-Mass m/Z 281/283 (M+H).
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