在EtSNa/DMF体系中,双键和溴代物不受影响;有时具有选择性去甲基化。
Typical Procedure.Dealkylation of m-Methoxytoluene. Ethanethiol (1.25 g, 11.8 mmol) dissolved in dry DMF (20 mL) is added to asuspension of sodium hydride (1.0 gof a 50% oil dispersion) in dry DMF (10 mL) under an atmosphere of nitrogen.The mixture is stirred for 5 min before solution of m-methoxytoluene (1.09 g) in dry DMF is added. The solutionis then refluxed for 3 hrs. The cooled mixture is acidified with 10% aqueoushydrochloric acid and extracted with ether. The ether layer is washed withwater and extracted with 5% sodium hydroxide. The alkaline extracts are thenacidified and reextracted with ether. The ethereal solution is washed withwater, dried and evaporated to give m-cresol as a light brown oil; yield: 0.85 g (78%).
【G. I. Feutrill and R.N. Mirrington, Tetrahedron Lett., 1970, 11, 1327. 】