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4-Bromo-1,2-dimethoxybenzene is a metabolite of bromobenzene, with a catechol moiety in the substructure. It also has use as a redox shuttle additive, essentially a component in lithium batteries that consumes excess current during overcharge. And also used in the synthesis of the isoquinoline alkaloid (-)-mesembrine.
Han Yu Xin.; Edward R. Biehl. Reaction of various nucleophiles with 2-bromo-p-xylene and 4-bromoveratrole via aryne reaction. J. Org. Chem. 1983, 48, (23), 4397-4399.
Timothy K. Beng.; Robert E. Gawley. Application of Catalytic Dynamic Resolution of N-Boc-2-lithiopiperidine to the Asymmetric Synthesis of 2-Aryl and 2-Vinyl Piperidines. Org. Lett. 1983, 13, (3), 394-397.
In the presence of sodamide, displacement by nucleophiles, e.g. anions of secondary amines or nitriles, occurs by an ortho-metallation-benzyne mechanism. The incoming nucleophile adds regioselectively such that the resulting anion is ortho-stabilized by methoxyl: J. Org. Chem., 48, 4397 (1983):
The derived Grignard reagent has been used in the synthesis of the isoquinoline alkaloid (-)-mesembrine: J. Org. Chem., 60, 6785 (1995).