反应详情

To a −40° C. solution of 2-bromo-4-nitro-anisole (1.16 g, 5 mmol) in THF (10 ml) was added vinylmagnesium bromide (1M in THF, 15 ml). The reaction mixture was stirred for 30 min while allowing the temperature to rise to −20° C. The reaction was quenched by addition of a saturated solution of NH4Cl, diluted with Et2O, and the aqueous layer was extracted twice with Et2O. The combined organic layers were dried over Na2SO4, filtered, concentrated, and purified via flash chromatography (hexane/EtOAc) to provide 4-bromo-5-methoxyindole XLVI (38 mg, 3% yield) as an oil.

1. customto rise to −20° C
2. customThe reaction was quenched by addition of a saturated solution of NH4Cl
3. additiondiluted with Et2O
4. extractionthe aqueous layer was extracted twice with Et2O
5. dry with materialThe combined organic layers were dried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated
8. custompurified via flash chromatography (hexane/EtOAc)