Benzenesulfonyl chloride → 4-Bromo-1-(phenylsulfonyl)-1H-indole
Reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.[H-].[Na+].[C:13]1([S:19](Cl)(=[O:21])=[O:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>O1CCCC1>[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][N:6]2[S:19]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)(=[O:21])=[O:20]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Under a nitrogen atmosphere, a solution of 4-bromo-1H-indole (200 g) in tetrahydrofuran (2.0 L) was ice-cooled to 0° C., and sodium hydride (49 g) was added thereto, followed by stirring under ice-cooling for 1 hour. Benzenesulfonyl chloride (200 g) was added dropwise under ice-cooling to the reaction mixture, and the ice bath was removed, followed by stirring at room temperature. A saturated aqueous ammonium chloride solution was added to the reaction mixture, followed by ethyl acetate extraction. The organic layer was washed with brine and dried over magnesium sulfate, followed by filteration. The resulting residue was washed with isopropylether-hexane (1:1, 1.0 L), and then dried to obtain the title compound (310 g) having the following physical properties.
Workup
- temperaturecooling for 1 hour
- temperaturecooling to the reaction mixture
- customthe ice bath was removed
- stirringby stirring at room temperature
- additionA saturated aqueous ammonium chloride solution was added to the reaction mixture
- extractionfollowed by ethyl acetate extraction
- washThe organic layer was washed with brine
- dry with materialdried over magnesium sulfate
- washThe resulting residue was washed with isopropylether-hexane (1:1, 1.0 L)
- customdried
Sources & evidence
- ORD record
- ord-b736b85dbbb84a10ab0ceafdd68c5a5c
- Source dataset
- uspto-grants-2012_02
- Patent number
- US08115014B2
Reaction notes
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