Sodium Methoxide → 6-Bromo-2-methoxyquinoline

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A solution of 2-chloro-6-bromoquinoline (4.0 g) in methanol (20 cm3) was heated under reflux with sodium methoxide [made from sodium (0.5 g) and methanol (20 cm3)] for 16 hours. The solvent was removed in vacuo and the residue was partitioned, between water (20 cm3) and chloroform (100 cm3). The aqueous phase was extracted wth chloroform (2×30 cm3) and the dried (MgSO4) organic extracts were evaporated to give a solid which was recrystallised from petroleum ether (b.p. 60°-80°) to yield the title compound, m.p. 93°-96°, (3.0 g).

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