The Journal of Organic Chemistry

Synthetic methods and reactions. 137. Ionic chlorination (bromination) of alkanes and cycloalkanes with methylene chloride (bromide)/antimony pentafluoride

GA Olah, AH Wu, O Farooq

Index: Olah, George A.; Wu, An-hsiang; Farooq, Omar Journal of Organic Chemistry, 1989 , vol. 54, # 6 p. 1463 - 1465

Full Text: HTML

Citation Number: 28

Abstract

(9b). To a solution of 2 g of dry 8 in 20 mL of dichloromethane were added 1 mL of distilled triethylamine, 1 g of tert-butyldi- methylsilyl chloride, and 100 mg of 4-(N,N-dimethylamino)- pyridine. The mixture was stirred at 25 "C for 18 h. The product was isolated by flash column chromatography on silica gel with 1:1 ethyl acetate/hexane to yield 1 g of the 5-0-silylated product 9a as a glassy solid: 'H NMR 0.15 (s, 6 H), 0.90 (m, 16 H), 1.10 (d, J = 7 Hz, 3 H), 1.15 (d, ...