Dichlorodimethylsilane → 4-Fluorophenyl(dimethyl)chlorosilane

Participants

Reaction Conditions

Reaction Steps

First, 6.45 g of dichlorodimethylsilane was dissolved in dry THF and cooled to 0° C. Next, 100 ml of 4-fluorobenzylmagnesium chloride (0.25 M) was slowly added dropwise thereto. After the completion of the addition, the reaction mixture was allowed to further react at low temperature for about 3 hours. Next, an excessive amount of hexane was added to the reaction mixture to precipitate a magnesium salt. The magnesium salt was removed via filtration and the organic solvent was evaporated under reduced pressure. By doing so, chlorodimethyl(4-fluorophenyl)silane was obtained with a yield of 80% via vacuum distillation. In a separate container, 3.0 g of 4-bromo-4′-n-propylbiphenyl and 250 mg of Mg was added to 20 ml of dry THF to provide a Grignard reagent, to which 2.3 g of chlorodimethyl(4-fluorophenyl)silane was added at room temperature. The reaction mixture was heated to 60° C. for about 10 hours, and worked up with water and hexane, and then purified by silica gel column chromatography to obtain the silicon-containing compound represented by the above formula (yield: 91%). 400 MHz 1H-NMR, CDCl3, δ (ppm): 0.30 (s, 6H), 0.99 (t, 3H), 1.65˜1.74 (m, 2H), 2.30 (s, 2H), 2.65 (t, 2H), 6.89 (d, 4H), 7.26˜7.28 (m, 2H), 7.50 (d, 2H), 7.54 (d, 2H), 7.58 (d, 2H).

Provenance & Evidence