4-Chlorophenol → HCID 58579933, compound

Participants

Reaction Steps

To a suspension of NaH (140 mg, 5.83 mmol) in anhydrous THF (150 mL) under N2 at RT was added dropwise 4-chlorophenol (738 mg, 5.74 mmol). After stirring the mixture at RT for 15 min, (chloromethyl)trimethylstannane (350 mg, 1.64 mmol) in anhydrous THF (5 mL) was added and the reaction was stirred at RT for 18 hours. The mixture was diluted with EtOAc (50 mL) and was washed with aqueous 1.0 N NaOH (3×60 mL). The EtOAc layer was dried over Na2SO4 and concentrated. The crude product was purified by flash chromatography (silica gel/hexane, using LC-MS to identify fractions containing the desire product) to afford ((4-chlorophenoxy)methyl)-trimethylstannane 8A (457 mg, 87% yield). 1H NMR (400 MHz, Chloroform-D) δ ppm 7.03 (2H, d, J=8.78 Hz), 6.67 (2H, d, J=9.03 Hz), 3.94 (2H, s), 0.00 (9H, s).

Provenance & Evidence