Potassium Carbonate → Methyl 4-bromo-1-benzothiophene-2-carboxylate

HRID 1098693

Reaction equation

HRID 1098693 reaction equation
Br[C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([Br:10])[C:3]=1[CH:4]=O.C(=O)([O-])[O-].[K+].[K+].[C:17]([O:21][CH3:22])(=[O:20])[CH2:18][SH:19]>CN(C=O)C>[CH3:22][O:21][C:17]([C:18]1[S:19][C:2]2[CH:9]=[CH:8][CH:7]=[C:6]([Br:10])[C:3]=2[CH:4]=1)=[O:20]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 16907Methyl ThioglycolateHCID 126486412,6-Dibromobenzaldehyde

Product 1

HCID 22473901Methyl 4-bromo-1-benzothiophene-2-carboxylateYield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To the solution of the compound (6.64 g, 25.16 mmol) obtained in Step 1 in DMF (90 ml), potassium carbonate (7.65 g, 55.35 mmol) and methyl thioglycolate (2.7 ml, 30.19 mmol) were added in that order, and then the reaction mixture was heated at reflux with stirring for 6 hours. After the termination of the reaction, the resulting reaction solution was cooled to room temperature, extracted with ethyl acetate, and then washed with water and brine. Subsequently, the reaction solution was dried over MgSO4, and then filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=40:1), thus obtaining the title compound as a white solid (5.72 g, 21.09 mmol, 84%).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux
  3. customAfter the termination of the reaction
  4. customthe resulting reaction solution
  5. extractionextracted with ethyl acetate
  6. washwashed with water and brine
  7. dry with materialSubsequently, the reaction solution was dried over MgSO4
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated under reduced pressure
  10. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=40:1)

Sources & evidence

ORD record
ord-0bf1638eb6c14b938a75455d8ccacaaa
Source dataset
uspto-grants-2012_03
Patent number
US08143307B2

Linked notes

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