Alkanethiolation process

Details Alkanethiolation process Alkanethiolation process

C - Chemistry, Metallurgy

07

C

C07C 321/28 (2006.01) C07C 319/14 (2006.01)

Patent

CA 2288448

A mixture formed from one or more alkyl disulfides, benzene, and at least about 1.5 equivalents of Lewis acid catalyst is heated to form alkanethiobenzene. Reaction in a mixture formed from excess benzene, dimethyldisulfide (DMDS) and AlCl3 in which the mole ratio of AlCl3 to DMDS was 2:1 was complete in 2 hours and afforded 98% conversion and 93% yield of thioanisole. In contrast, the same reaction when attempted using a 1:1 mole ratio of AlCl3 to DMDS after 6 hours achieved only 66% conversion and a thioanisole yield of only 35%. So far as is known, this is the first example of a highly efficient electrophilic aromatic substitution of the inactivated benzene ring by an alkanethio group.

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