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

HRID 1098693

반응식

HRID 1098693 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-0bf1638eb6c14b938a75455d8ccacaaa
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08143307B2

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