Quinoline → 6-Bromo-benzo[b]thiophene

Participants

Reaction Conditions

Reaction Steps

To quinoline (45 ml) were added 6-bromobenzothiophene -2-carboxylic acid (14 g) and copper powder (874 mg), followed by stirring under heat at an oil temperature of 220° C. for 2 hours. After the reaction mixture was allowed to cool down, ether was added and the copper powder was filtered off. The filtrate was washed with a 1N aqueous solution of hydrochloric acid, then with a 1N aqueous solution of sodium hydroxide and finally with saturated aqueous NaCl solution, followed by drying over anhydrous sodium sulfate. The solvent was then distilled off under reduced pressure. The residue was purified by chromatography on a silica gel column (hexane), whereby the title compound (5.56 g) was obtained as a pale yellow solid. In addition, the raw material (3.15 g) was recovered.

Provenance & Evidence