反应详情

Methyl 4-hydroxy-1,2,3,4-tetrahydronaphthalene-1-carboxylate (3.68 g, 17.84 mmol) was taken-up in dichloromethane (17.8 ml) and the solution was purged and then evacuated with argon. Phosphorus tribromide (3.4 ml, 36 mmol) was added, and the resulting mixture was allowed to stir at room temperature over the weekend. The reaction was diluted with aqueous sodium bicarbonate and product was extracted with dichloromethane (3×). The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (0 to 100% EtOAc/hexanes) to afford racemic methyl 4-bromo-1,2,3,4-tetrahydronaphthalene-1-carboxylate as a light yellow oil.

1. customthe solution was purged
2. customevacuated with argon
3. extractionwas extracted with dichloromethane (3×)
4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
5. concentrationconcentrated under reduced pressure
6. customThe residue was purified by column chromatography on silica gel (0 to 100% EtOAc/hexanes)