CHLOROMETHYL METHYL SULFIDE

Chemical Properties

CLEAR YELLOW TO BROWN LIQUID

Uses

Methylthiomethylating reagent for carbonyl and aromatic compounds. Methylene transfer reagent for iron(II) mediated cyclopropanation.

Uses

Chloromethyl methyl sulfide is used as a methylene transfer reagent for iron(II) mediated cyclopropanation and for carbonyl and aromatic compounds. It protects alcohols as their methylthiomethyl (MTM) ethers by reaction, e.g. with NaH/NaI in DME. It is also used for the preparation of MTM esters of carboxylic acids, e.g. by treatment of the K salt of the acid in the presence of NaI and 18-crown-6 and for reaction with cyclopentadienyl iron dicarbonyl dimer in the formation of an iron-containing methylene transfer agent.

Synthesis Reference(s)

Tetrahedron Letters, 35, p. 6127, 1994 DOI: 10.1016/0040-4039(94)88094-8