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).