Forced nucleophilic substitution reaction of chlorobenzenes bearing electron-donating groups by the use of "naked" methoxide anion.

Nucleophilic aromatic substitution reactions of chlorobenzenes with the methoxide anion were found to proceed smoothly even in cases where electron-donating groups were present in the same aromatic ring when the chlorobenzenes were activated by chromium tricarbonyl complex formation and when the effectiveness of the methoxide anion was enhanced by the use of 18-crown-6. Application of the present method to indoline or tetrahydroquinoline systems was then examined and 5-chloro-1, 3, 3-trimethylindoline was successfully converted to the corresponding 5-methoxy or 5-benzyloxy compound.