Benzenesulfonyl chloride → 1-(benzenesulfonyl)-4-bromo-6-fluoro-1H-indole

HRID 1159785Notes

Reaction equation

HRID 1159785 reaction equation
[OH-].[Na+].[Br:3][C:4]1[CH:12]=[C:11]([F:13])[CH:10]=[C:9]2[C:5]=1[CH:6]=[CH:7][NH:8]2.[C:14]1([S:20](Cl)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl>[Br:3][C:4]1[CH:12]=[C:11]([F:13])[CH:10]=[C:9]2[C:5]=1[CH:6]=[CH:7][N:8]2[S:20]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(=[O:22])=[O:21]

Participants

6

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 247281734-Bromo-6-fluoro-1H-indole3×

Product 1

HCID 687161141-(benzenesulfonyl)-4-bromo-6-fluoro-1H-indoleYield 130.3%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

Aq. 4 M NaOH (5 mL) was added to a stirring mixture of 4-bromo-6-fluoro-1H-indole (500 mg, 2.34 mmol; Intermediate 35), benzenesulfonyl chloride (329 μL g, 2.57 mmol) and tetrabutylammonium hydrogen sulfate (78 mg, 0.23 mmol) in DCM (30 mL). The reaction mixture was stirred 1 h, combined with an earlier batch of this intermediate (followed this experimental and starting with 4-bromo-6-fluoro-1H-indole, 152 mg, 0.71 mmol; Intermediate 35), washed twice with water, dried and concentrated. The product (1.08 g, 100%) was obtained as a beige solid. MS (ESI+) for C14H9BrFNO2S m/z 354 (M+H)+.

Workup

  1. washIntermediate 35), washed twice with water
  2. customdried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-bf922ae7970c4c25b4f5ca2f6ecdba4e
Source dataset
uspto-grants-2010_10
Patent number
US07812017B2

Reaction notes

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