Potassium Carbonate → 1-(3-Bromophenyl)-2,5-dihydro-1H-pyrrole

HRID 2216354Notes

Reaction equation

HRID 2216354 reaction equation
CS(O[CH2:6]/[CH:7]=[CH:8]\[CH2:9]OS(C)(=O)=O)(=O)=O.[Br:15][C:16]1[CH:17]=[C:18]([CH:20]=[CH:21][CH:22]=1)[NH2:19].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Br:15][C:16]1[CH:17]=[C:18]([N:19]2[CH2:9][CH:8]=[CH:7][CH2:6]2)[CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 115623-BromoanilineHCID 64333312-Butene-1,4-diol, 1,4-dimethanesulfonate, (2Z)-

Product 1

HCID 177499441-(3-Bromophenyl)-2,5-dihydro-1H-pyrroleYield 50.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Then, a mixture of 15 g of the cis-1,4-bis(methanesulfonyloxy)-2-butene, 10 g of 3-bromoaniline, 24 g of anhydrous potassium carbonate and 70 ml of N,N-dimethylformamide was stirred at room temperature overnight. The reaction mixture was extracted with ethyl acetate-water, and the organic layer was washed with water and brine, dried over anhydrous magnesium sulfate and then evaporated. The residue was purified by silica gel column chromatography with 5% ethyl acetate/hexane, to give 6.6 g of the title compound.

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate-water
  2. washthe organic layer was washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated
  5. customThe residue was purified by silica gel column chromatography with 5% ethyl acetate/hexane

Sources & evidence

ORD record
ord-e1e4bcd2a4024edabdae7d4ba268d923
Source dataset
uspto-grants-2006_09
Patent number
US07112593B2

Reaction notes

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