Reagent for the high-yield thiomethylation of O-silylated lactone and ester enolates in the synthesis of α-methylene lactones and esters.1
Reagent for the high-yield thiomethylation of O-silylated lactone and ester enolates in the synthesis of α-methylene lactones and esters.
The two most convenient methods of chloromethyl phenyl sulfide are the reaction of Thioanisole with Sulfuryl Chloride and the reaction of Thiophenol with bromochloromethane using 1,8-Diazabicyclo[5.4.0]undec-7-ene or an alkali metal hydroxide as the base.
Chloromethyl phenyl sulfideshould be handled in a well-ventilated fume hood and kept cooled. Freshly prepared material can be stored at 0-5 °C without any appreciable decomposition. It is advisable to use freshly prepared or distilled material for reactions.
Dissolve the sulfide in CH2Cl2 or CCl4 and dry it (CaCl2), or pass it through a tube of CaCl2 and distil it using a fractionating column. Harmful vapours. It gives the sulfone [7205-98-3] (b 130o/1mm and m 53o from EtOH) [Beilstein 6 IV 1507] on oxidation with permonophthalic acid. [B.hme et al. Justus Liebigs Ann Chem 563 54 64 1949.] [Beilstein 6 III 1002.]
