Tetrahydrofuran → 3,6-dibromo-9-((oxiran-2-yl)methyl)-9H-carbazole
Reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:6][C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][C:10]([Br:15])=[CH:9][CH:8]=3.[H-].[Na+].[CH2:18]1[CH2:22][O:21][CH2:20]C1>>[Br:15][C:10]1[CH:9]=[CH:8][C:7]2[N:6]([CH2:18][CH:22]3[CH2:20][O:21]3)[C:5]3[C:13]([C:12]=2[CH:11]=1)=[CH:14][C:2]([Br:1])=[CH:3][CH:4]=3Participants
4
Procedure
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.
Workup
- customis quenched with a saturated aqueous solution of sodium hydrogenocarbonate (200 mL)
- extractionExtraction with Et2O (500 mL+2×250 mL)
- dry with materialdrying over MgSO4 and evaporation under reduced pressure
- customgives a yellow solid
Sources & evidence
- ORD record
- ord-088cfe55fdcf4aed9d0e1b1d8a7542ca
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08053436B1
Reaction notes
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