Allyl bromide → HCID 22406568, compound

HRID 440272Notes

Reaction equation

HRID 440272 reaction equation
[N+:1]([C:4]1[S:5][CH:6]=[C:7]([C:9]([OH:11])=[O:10])[CH:8]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].[CH2:18](Br)[CH:19]=[CH2:20]>CN(C=O)C.O>[N+:1]([C:4]1[S:5][CH:6]=[C:7]([C:9]([O:11][CH2:20][CH:19]=[CH2:18])=[O:10])[CH:8]=1)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 27772675-nitrothiophene-3-carboxylic acid

Product 1

HCID 22406568HCID 22406568, compoundYield 79.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

2-Nitro-4-thiophenecarboxylic acid (2.5 g, 14.45 mmol) was suspended in DMF (25 ml) in the presence of potassium carbonate (4 g, 28.9 mmol) at ambient temperature. Allyl bromide (5 ml, 57.8 mmol) was added to this solution and the mixture stirred at ambient temperature overnight. The mixture was diluted with water and extracted with ethyl acetate. After concentration, the residue was purified by silica gel chromatography using ethyl acetate/petroleum ether as eluant (10:30) to give the title compound (2.45 g, 77%).

Workup

  1. extractionextracted with ethyl acetate
  2. concentrationAfter concentration
  3. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-b3e736227c084e31ba0ccfd55eac0d20
Source dataset
uspto-grants-1996_05
Patent number
US05519015

Reaction notes

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