Water → 3-Bromo-1-(P-toluenesulfonyl)indole
Reaction equation
[Br:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][CH:3]=1.[S:11](Cl)([C:14]1[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=1)(=[O:13])=[O:12].[OH-].[Na+].O>C1C=CC=CC=1.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[Br:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([S:11]([C:14]2[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=2)(=[O:13])=[O:12])[CH:3]=1Participants
Procedure
To a solution of 3-bromoindole (prepared according to the method described in Synthesis, 1096(1982)) (196 mg, 1.0 mmol) and tosyl chloride (286 mg, 1.5 mmol) in benzene (4.5 mL) was added tetra-n-butylammonium hydrogensulfate (34 mg, 0.1 mmol) and a 5.0% aqueous sodium hydroxide (1.0 mL), and the resulting mixture was refluxed for 1 hour. After the reaction solution was cooled to room temperature, water was added to the reaction solution, and the resulting mixture was extracted with chloroform. After drying over anhydrous sodium sulfate, the chloroform layer was concentrated, and the resulting crude product was purified by column chromatography on a silica gel (eluent; hexane:ethyl acetate=6:1) to afford the title compound (335 mg, yield: 96%) as white crystals.
Workup
- extractionthe resulting mixture was extracted with chloroform
- dry with materialAfter drying over anhydrous sodium sulfate
- concentrationthe chloroform layer was concentrated
- customthe resulting crude product was purified by column chromatography on a silica gel (eluent; hexane:ethyl acetate=6:1)
Sources & evidence
- ORD record
- ord-d4eccb9a4fc145d0b357794e9d169fb4
- Source dataset
- uspto-grants-2003_11
- Patent number
- US06642228B1
Reaction notes
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