[Li]CCCC.[Cl:6][C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[C:9]([F:14])[CH:8]=1.Cl[Si:16]([CH3:19])([CH3:18])[CH3:17]>C1COCC1>[Cl:6][C:7]1[CH:12]=[C:11]([F:13])[C:10]([Si:16]([CH3:19])([CH3:18])[CH3:17])=[C:9]([F:14])[CH:8]=1A solution of 2.5M n-BuLi in hexanes (60 ml, 0.15 mol) was added dropwise to a solution of 1-chloro-3,5-difluorobenzene (19.2 g, 0.13 mol) in THF (200 mL) cooled to −70° C. under Ar. After the addition was complete, the mixture was stirred for 1 h before a solution of chlorotrimethylsilane (21.7 g, 0.2 mol) in THF (25 mL) was added dropwise. The reaction was allowed to warm to rt with stirring overnight before cooling and quenching with H2O. The phases were separated and pentane (200 mL) was added; after washing with H2O the solution was dried over MgSO4 and carefully concentrated in vacuo to yield the title compound as a solution in THF (46 g) which was in the next step without further purification.
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