N-Butylchlorodimethylsilane → (4-Bromophenylethynyl)-n-butyldimethylsilane

Participants

Reaction Steps

i-propylmagnesiumbromide (0.67 M/THF solution, 3.10 mL, 2.1 mmol) was added dropwise to THF solution (15 mL) of 1-bromo-4-ethynylbenzene (382 mg, 2.0 mmol) at 0° C. After the mixture was stirred for 20 minutes, an ice water bath was removed. After stirring at room temperature for 10 minutes, n-butyldimethylsilyl chloride (0.69 mL, 4.0 mmol) was added to the mixture. After stirring for 2 hours, the reaction was terminated by the addition of saturated ammonium chloride solution (5 mL). The reaction mixture was extracted with ethyl acetate, and it was concentrated and thereafter purified by means of flash column chromatography to obtain (4-bromophenylethynyl)-n-butyldimethylsilane (530 mg, isolated yield: 90%).

Provenance & Evidence