Bromoacetylium Hexafluoroantimonate

BrCH2CO+SbF6-

[54854-60-3]  · C2H2BrF6OSb  · Bromoacetylium Hexafluoroantimonate  · (MW 357.68)

(bromoacetylating agent)

Physical Data: mp 82 °C.

Preparative Method: prepared by treating BrCH2COF with antimony pentafluoride in Freon 113.1a Pure BrCH2CO+SbF6- is obtained by washing the crude product with excess dry Freon 113.

Handling, Storage, and Precautions: corrosive and moisture sensitive. Store in a Teflon or a Nalgene bottle under anhydrous conditions. Use in a fume hood.

Bromoacetylium hexafluoroantimonate has been used to bromoacetylate aromatic compounds (eq 1). It reacts readily with benzene, toluene, p-xylene, and mesitylene to generate the corresponding bromoacylated products in high yields. In the case of toluene a 3.8:31.1:95.1 isomer distribution ratio is obtained for the ortho, meta, and para isomers.1b


1. (a) Olah, G. A.; Lin, H. C.; Germain, A. S, 1974, 895. (b) Olah, G. A.; Germain, A.; Lin, H. C. JACS 1975, 97, 5481.

George A. Olah, G. K. Surya Prakash, Qi Wang, & Xing-ya Li

University of Southern California, Los Angeles, CA, USA



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