Water → 5-Bromothiophene-3-carboxylic acid

HRID 1351320Notes

Reaction equation

HRID 1351320 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([C:6]([OH:8])=[O:7])=[CH:2]1.[Br:9]N1C(=O)CCC1=O.O>CN(C)C=O>[Br:9][C:5]1[S:1][CH:2]=[C:3]([C:6]([OH:8])=[O:7])[CH:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6918Thiophene-3-carboxylic acidHCID 67184N-bromobutanimide

Product 1

HCID 120399785-Bromothiophene-3-carboxylic acidYield 54.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of thiophene-3-carboxylic acid (18.2 g) in N,N-dimethylformamide (250 mL) was added N-bromosuccinimide (27.8 g) in small amounts on an ice bath. After stirring at room temperature overnight, the reaction solution was poured into water (1.5 L), and the resulting solid was collected by filtration and washed with water. After dissolving in ethyl acetate, and dried with anhydrous magnesium sulfate, the drying agent was removed by filtration, and evaporation in vacuo was carried out. The solid that was generated by dissolving the residue in ethyl acetate, and adding hexane were collected by filtration, and the crude product (16 g) of 5-bromo-thiophene-3-carboxylic acid was obtained as a colorless solid.

Workup

  1. filtrationthe resulting solid was collected by filtration
  2. washwashed with water
  3. dissolutionAfter dissolving in ethyl acetate
  4. dry with materialdried with anhydrous magnesium sulfate
  5. customthe drying agent was removed by filtration, and evaporation in vacuo
  6. dissolutionby dissolving the residue in ethyl acetate
  7. additionadding hexane
  8. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-16d96b6733cb48e7ae3f5d178aca28f5
Source dataset
uspto-grants-2007_05
Patent number
US07217723B2

Reaction notes

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