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Benzenesulfonyl chloride → HCID 67240891, compound

HRID 2423115
Notes
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Reaction equation

HRID 2423115 reaction equation
[Br:1][C:2]1[C:10]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.[C:19]1([S:25](Cl)(=[O:27])=[O:26])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[OH-].[Na+]>C(Cl)Cl.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[Br:1][C:2]1[C:10]([O:11][CH2:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][N:6]2[S:25]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)(=[O:27])=[O:26]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 672408605-Benzyloxy-4-bromo-1H-indole2×

Product 1

HCID 67240891HCID 67240891, compoundYield 101.5%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalyst
HCID 6344
Dichloromethane
Solvent

Procedure

To a solution of 4-bromo-5-benzyloxy-1H-indole (Intermediate 2, 3.85 g, 12.7 mmol) in DCM (30 mL) was added benzenesulfonyl chloride (2.47 g, 14.0 mmol), tetrabutylammonium hydrogensulphate (0.41 g, 1.3 mmol) and 3 M NaOH (13 mL, 39 mmol) and the mixture was stirred vigorously at room temperature for 30 minutes. The organic phase was washed with water and brine, dried (MgSO4) and concentrated to dryness to give the title compound (5.7 g) as a solid. MS m/z 442/444 [M+H]+.

Workup

  1. washThe organic phase was washed with water and brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-5ce77bac43044f9fb566d899aaf52fd8
Source dataset
uspto-grants-2011_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07960374B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes