Water → Ethyl 5-bromothiophene-2-carboxylate

HRID 1181601Notes

Reaction equation

HRID 1181601 reaction equation
[Br:1][C:2]1[S:6][C:5]([C:7]([OH:9])=[O:8])=[CH:4][CH:3]=1.[CH2:10](N=C=NCCCN(C)C)[CH3:11].O>C(O)C.CN(C)C1C=CN=CC=1>[Br:1][C:2]1[S:6][C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 962WaterHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 3491155-Bromothiophene-2-carboxylic acid

Product 1

HCID 605723Ethyl 5-bromothiophene-2-carboxylateYield 97.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 702EthanolSolvent

Procedure

5-Bromothiophene-2-carboxylic acid (5.40 g) was dissolved in ethanol (50 ml), 4-dimethylaminopyridine (3.82 g) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (6.0 g) were successively added, and the mixture was stirred overnight at room temperature. Water was added to the reaction mixture, and the mixture was extracted 3 times with ethyl acetate. The organic layer was washed successively with water, 10% aqueous citric acid (twice), water, saturated aqueous sodium hydrogencarbonate and brine, and dried over sodium sulfate. The organic layer was concentrated under reduced pressure to give the title compound (5.99 g).

Workup

  1. extractionthe mixture was extracted 3 times with ethyl acetate
  2. washThe organic layer was washed successively with water, 10% aqueous citric acid (twice), water, saturated aqueous sodium hydrogencarbonate and brine
  3. dry with materialdried over sodium sulfate
  4. concentrationThe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-b9b79a29da9b4986b163a808db9e27fc
Source dataset
uspto-grants-2007_10
Patent number
US07285572B2

Reaction notes

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