Thionyl Chloride → HCID 22574076, compound

Participants

Reaction Steps

Following a procedure similar to that reported by Greenhouse et al., J. Org. Chem. 53 (1988) 2634, a solution of (5-chloro-3-methanesulfinyl-indol-1-yl)-acetonitrile (0.851 g, 3.38 mmole) in methylene chloride (85 ml) was cooled to 0° C. and solid sodium bicarbonate (3.66 g) was added. Thionyl chloride (0.422 g, 3.55 mmole) was dissolved in methylene chloride and added dropwise over a 45 minute period. Upon termination of addition, the reaction mixture was stirred an additional 15 m. Tlc analysis revealed the presence of a small amount of starting material. Additional thionyl chloride was added, one drop at a time until tlc analysis revealed the total consumption of starting material. When no more starting material was present, the entire reaction mixture was poured onto a short silica gel column and the product was eluted with methylene chloride and isolated by evaporation of the solvent to afford 0.657 g (72%) pure (2,5-dichloro-3-methylsulfanyl-indol-1-yl)-acetonitrile.

Provenance & Evidence