chloromethyl phenyl sulfide

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Properties of substance:

chloromethyl phenyl sulfide

Group of substances:

organic

Empirical formula (Hill's system for organic substances):

C₇H₇ClS

Structural formula as text:

C6H5SCH2Cl

Synthesis 1:

Reference: Bordwell, F. G., Pitt, B. M. The Formation of α-Chloro Sulfides from Sulfides and from Sulfoxides / Journal of the American Chemical Society. - 1955. - Vol. 77, No. 3 pp. 577 [doi: 10.1021/ja01608a016]

C₆H₅SOC₆H₅ + C₆H₅CH₂SCH₃ + SOCl₂ → C₆H₅SC₆H₅ + C₆H₅CHClSCH₃ + SO₂ + HCl

A solution of 40.5 g. (0.20 mole) of phenyl sulfoxide and 24.8 g. (0.20 mole) of methyl phenyl sulfide in 75 ml. of methylene chloride was added to a heated solution of 26.4 g. (0.22 mole) of thionyl chloride in 40 ml. of methylene chloride during 90 minutes. The mixture was distilled under vacuum, giving first 18.4 g. (58%) of chloromethyl phenyl sulfide, b.p. 78—80° (2 mm.), and then 24.2 g. (65%) of phenyl sulfide, b.p. 115—116° (2 mm.).

Synthesis 2:

A solution of 28 g. (0.20 mole) of methyl phenyl sulfoxide in 40 ml. of methylene chloride was added during 2 hours to a heated solution of 27 g. (0.23 mole) of thionyl chloride in 40 ml. of methylene chloride. The solution was refluxed for an additional hour and distilled giving 29.3 g. (92%) of chloromethyl phenyl sulfide, b.p. 99—101° (7 mm.).

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