Hydrogen Bromide → HCID 60155616, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of compound (29a) (3.0 g, 13.9 mmol) in 40% hydrobromic acid (8.0 mL, 54.4 mmol), an aqueous solution (17 mL) of sodium nitrite (1.1 g, 15.7 mmol) was added dropwise under stirring at 0 to 5° C. The solution was allowed to reach room temperature. To the solution, CuBr (1.1 g, 11.2 mmol) and 96% sulfuric acid (0.1 mL) were added, and the mixture was refluxed under stirring for 1 hour. After cooling and subsequent extraction with ethyl acetate, the obtained residue was dissolved in methanol (50 mL). To the obtained mixture, a catalytic amount of concentrated hydrochloric acid (0.1 mL) was added and refluxed for 3 hours. After cooling, the solvent was distilled off and the obtained product was treated with ether (50 mL). The organic layer was dried (over sodium sulfate) and the solvent was distilled off. The obtained residue was subjected to silica gel column chromatography and elution with an n-hexane/ethyl acetate (4:1) solution to give 3.01 g (73%) of compound (30a) as pale yellow liquid matter.

Provenance & Evidence