Chlorotrimethylsilane → Benzonitrile, 3-fluoro-6-methyl-2-(trimethylsilyl)-

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Reaction Conditions

Reaction Steps

n-Butyllithium (1.40M in hexanes, 11.8 mmol, 8.44 ml) was added dropwise to a stirred solution of diisopropylamine (1.84 ml) in THF (5 ml) at 0° C. After 30 min., the solution was cooled to -78° C. and 3-fluoro-6-methylbenzonitrile (1.60 g, 11.8 mmol) in THF (5 ml) was added dropwise. The pale purple anion was stirred for 20 min., trimethylsilylchoride (3.0 ml, 24 mmol) was added and the mixture warmed to room temperature over 1 h, evaporated, the residue taken up in a small amount of diethyl ether and filtered. Evaporation of the filtrate gave an off-white crystalline solid (2.3 g), m.p. 71-73° C.

Provenance & Evidence