Preparation of Thiol Esters – DMAP as Catalyst

S.Kim and S.Yang, Chem. Lett., 133, (1981)

  1. To a solution of benzoic acid (123 mg, 1.0 mmol), 1-fluoro-2,4,6-trinitrobenzene (235 mg, 1.0 mmol), and DMAP (249 mg, 2.0 mmol) in acetonitrile (4 mL) is added tert-butanethiol (98 mg, 1.1 mmol).

  2. The reaction mixture is stirred at ambient temperature for 4 h. 

  3. The precipitated salts are filtered off, the solution concentrated, the residue purified by filtration through a short column of silica gel (eluent dichloromethane) followed by evaporation of the solvent to afford the thiol ester (184 mg, 95%).

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Acylation

Tertiary Thiol