Benzenesulfonyl chloride → HCID 68715889, compound

HRID 1159792Notes

Reaction equation

HRID 1159792 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.[C:13]1([S:19](Cl)(=[O:21])=[O:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[OH-].[Na+]>C(Cl)Cl.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[Br:1][C:2]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[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

6

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 468355404-Bromo-7-methoxy-1H-indole

Product 1

HCID 68715889HCID 68715889, compound

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

4-Bromo-7-methoxy indole (2 g, 8.8 mmol) was dissolved in CH2Cl2 (300 mL). PhSO2Cl (2.4 g, 9.4 mmol was added, followed by tetrabutylammonium hydrogen sulfate (0.34 g, 0.88 mmol) and 4M aqueous NaOH (17 mL), in that order. The reaction mixture was stirred at ambient temperature for 3 hrs. The layers were separated and the aqueous layer was extracted with CH2Cl2, washed with H2O, dried over Na2SO4, filtered and concentrated. The crude material was recrystallised from ethanol to give 4-bromo-7-methoxy-1-(phenylsulfonyl)-1H-indole, 0.9 g.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with CH2Cl2
  3. washwashed with H2O
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude material was recrystallised from ethanol

Sources & evidence

ORD record
ord-0c58c7c8526242549beadcf543a15c03
Source dataset
uspto-grants-2010_10
Patent number
US07812017B2

Reaction notes

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