1,2-dichloro-3-(methylthio)benzene synthesis

Yield:17733-25-4 72%

Reaction Conditions:

with sodium hydroxide in hexane at 0 - 110; for 2 h;

Steps:

26A

Example 26A 2, 3-DICHLORO-4-METHYLSULFANYL-BENZENE Dimethyl sulfate (2.90 mL, 30.7 mmol) was added dropwise to a stirred solution of NaOH (1.28 g, 32.1 mmol) and 2,3-dichlorobenzenethiol (5.00 g, 27.9 mmol) in water (50 ML) at 0°C. The reaction mixture was heated at 110°C for 2 h. After cooling, the reaction mixture was extracted with ether. The organic layer was washed with water and brine, dried, and filtered. Evaporation of the solvent followed by recrystallization from hexane gave the title compound (3.89 g, 72%) as a white SOLID. 1H NMR (CDC13, 400 MHz) 5 7.24 (dd, J=8.2 Hz, J=1.6 Hz, 1H), 7.18 (t, J=8.2 Hz, 1H), 7.04 (dd, J=8.2 Hz, J=1.6 Hz, 1H), 2.48 (s, 3H).

References:

WO2005/16883,2005,A2 Location in patent:Page/Page column 169