Chlorotrimethylsilane → Silane, [[1-(4-fluorophenyl)ethenyl]oxy]trimethyl-

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Reaction Steps

Under nitrogen, 17.7 g (128 mmol) of 4-fluoroacetophenone (Aldrich) and 20.7 mL (192 mmol) of triethylamine at ambient temperature was treated with 24.4 mL (192.3 mmol) of chlorotrimethylsilane and allowed to stir of 20 minutes prior to the slow addition of a suspension of 30 g (200 mmol) of sodium iodode in 200 mL of acetonitrile. The extracts were combined, dried (K2CO3), and concentrated in vacuo to give 27 g of crude 1-fluoro-4-[1[(trimethylsilyl)oxy]ethenyl]benzene as an oil: NMR (CDCl3) δ0.28 (s, 9H), 4.41 (d, J=2 Hz, 1H), 4.84 (d, J=2 Hz, 1H), 7.00 (d, J=8 Hz, 2H), 7.53-7.60 (m, 2H).

Provenance & Evidence