Sodium Chloride → 1-[(4-bromophenyl)sulfonyl]-1H-indole-2-carbaldehyde

HRID 2264627Notes

Reaction equation

HRID 2264627 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=[C:12]2[CH2:20][OH:21])(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(N(CC)CC)C.[Cl-].[Na+]>ClCCCl.CS(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=[C:12]2[CH:20]=[O:21])(=[O:9])=[O:10])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 5234Sodium ChlorideHCID 8471TriethylamineHCID 67044165{1-[(4-bromophenyl)sulfonyl]-1H-indol-2-yl}methanol

Product 1

HCID 442108071-[(4-bromophenyl)sulfonyl]-1H-indole-2-carbaldehydeYield 98.4%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 0.93 g of {1-[(4-bromophenyl)sulfonyl]-1H-indol-2-yl}methanol and 1.1 mL of triethylamine in 10 mL of 1,2-dichloroethane, a solution of 1.21 g of sulfur trioxide-pyridine complex in 5 mL of DMSO was added under ice cooling, and the resulting mixture was stirred under ice cooling for 1 hour. The solution was poured into a mixed solution of 25 ml of ice water and 25 mL of saturated aqueous sodium chloride solution, the resulting mixture was extracted with 100 mL of ethyl acetate, the extract was washed with 5% aqueous potassium hydrogen sulfate solution, water and saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was washed with hexane to obtain 0.91 g of 1-[(4-bromophenyl)sulfonyl]-1H-indole-2-carbaldehyde as a beige solid. FAB+: 364, 366

Workup

  1. extractionthe resulting mixture was extracted with 100 mL of ethyl acetate
  2. washthe extract was washed with 5% aqueous potassium hydrogen sulfate solution, water and saturated aqueous sodium chloride solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. washThe residue was washed with hexane

Sources & evidence

ORD record
ord-a18ca397aefb404880692ac250803299
Source dataset
uspto-grants-2010_12
Patent number
US07855225B2

Reaction notes

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