Water → HCID 87077397, compound

Participants

Reaction Conditions

Reaction Steps

To a reaction container equipped with a dropping funnel, 21.6 g of 2,5-dibromopyridine and 243 mL of diethyl ether were added. The obtained solution was cooled at −70° C. and then, 55.26 mL of butyl lithium (1.65 M/hexane solution) was added dropwise thereto. The obtained mixture was stirred for 3 hours and 10 minutes and then, a solution obtained by dissolving 20.96 mL of tert-butyldimethylsilyl trifluoromethanesulfonate in 16.7 mL of diethyl ether was added dropwise thereto. The obtained mixture was stirred for 17 hours and 55 minutes and then, 162 mL of water was added dropwise thereto at 0° C. The obtained mixture was stirred at room temperature for 30 minutes and then, 81 mL of ethyl acetate was added thereto. The obtained solution was extracted three times with 81 mL of ethyl acetate. The obtained organic layers were mixed and dried with magnesium sulfate. After removing magnesium sulfate by filtration, the filtrate was concentrated to obtain a crude product. The crude product was purified with silica gel column chromatography followed by further recrystallization with hexane to obtain 2.57 g of 2-bromo-5-tert-butyldimethylsilylpyridine. Purity: 98% (area percentage value obtained by gas chromatography analysis).

Provenance & Evidence