I am carrying out a thiomethylation of an aromatic ring, using dimethyl disulphide (MeS-SMe) as the electrophile to react with an aryllithium compound. The released methanethiolate anion is captured by adding methyl acrylate (the Michael adduct of which is then hydrolysed and washed into water).
The current method works fine, except I end up with too much polymeric material in the isolated product. I assume the acrylate plays a big part in producing the polymerics.
Anybody who has a smarter and cleaner way of trapping methylthiolate?