[Archer]

I need to synthesise 4-acetylthioanisole (SMILE below) and I have very little experience of thioethers and their respective stability.
CSc1ccc(cc1)C(C)=O

I intend to use the ever reliable Friedel-Crafts (FC) Acylation but just wanted to see if anyone has any experience of this particular substance under FC conditions. For example, is the C-S bond labile in the presence of AlCl₃ ?

I have had issues with FC reactions on certain substrates before which have resulted in unwanted products and / or residues in the flask which are difficult to remove. I had particular difficulty with 2-acetylthiophene, which not only gave a low yield but the black tar-like product / bi-products mix smelled very bad indeed.

Thanks in advance for any experiences you can share with me.

[sjb]

I need to synthesise 4-acetylthioanisole (SMILE below) and I have very little experience of thioethers and their respective stability.

I intend to use the ever reliable Friedel-Crafts (FC) Acylation but just wanted to see if anyone has any experience of this particular substance under FC conditions. For example, is the C-S bond labile in the presence of AlCl₃ ?

I have had issues with FC reactions on certain substrates before which have resulted in unwanted products and / or residues in the flask which are difficult to remove. I had particular difficulty with 2-acetylthiophene, which not only gave a low yield but the black tar-like product / bi-products mix smelled very bad indeed.

Thanks in advance for any experiences you can share with me.

The supplementary material (part 2) to Jereb, Green Chem. 2012, 14, 3047-52 (http://dx.doi.org/10.1039/C2GC36073J) suggests this isn't a problem