Tetrahydrofuran → 3,6-dibromo-9-((oxiran-2-yl)methyl)-9H-carbazole

Participants

Reaction Steps

At rt a solution of 3,6-dibromo-9H-carbazole (5.23 g, 16.10 mmol) in anhydrous THF (200 mL) is treated with NaH (0.703 g, 16.10 mmol, 55% in mineral oil) and a solution of (±)-3-nitro-benzene sulfonic acid oxiranyl methyl ester (4.17 g, 16.10 mmol) in anhydrous THF (30 mL). After 16 hours of stirring at rt the reaction mixture is quenched with a saturated aqueous solution of sodium hydrogenocarbonate (200 mL). Extraction with Et2O (500 mL+2×250 mL), drying over MgSO4 and evaporation under reduced pressure gives a yellow solid. Flash chromatography on a 7×27 cm2 column of SiO2 using DCM/Petroleum Ether (1/1) gives the title compound (3.65 g, 9.58 mmol) as a white solid in a 59% yield.

Provenance & Evidence