Regioselective bromination of 1,4-dimethoxy-2,3-dimethylbenzene and conversion into sulfur-functionalised benzoquinones

The NBS bromination of 1,4-dimethoxy-2,3-dimethylbenzene has been examined under a variety of conditions in both 1,1,1-trichloroethane and benzotrifluoride. Four different bromination products have been isolated including the previously unknown 1-bromo-4-bromomethyl-2,5-dimethoxy-3-methylbenzene whose single crystal X-ray structure is presented. The synthetically useful 2,3-bis(bromomethyl)-1,4-dimethoxybenzene is readily prepared using either solvent and it has been converted into new sulfur-containing quinone derivative