Ethanol → 3,3'-Dibromo-2,2'-bithiophene

HRID 278831노트

반응식

HRID 278831 반응식
[Br:1][C:2]1[CH:6]=[C:5](Br)[S:4][C:3]=1[C:8]1[S:9][C:10](Br)=[CH:11][C:12]=1[Br:13].C(O)C.O>[Zn].C(O)(=O)C>[Br:13][C:12]1[CH:11]=[CH:10][S:9][C:8]=1[C:3]1[S:4][CH:5]=[CH:6][C:2]=1[Br:1]

참가 물질

6

반응물 3

HCID 702EthanolHCID 962WaterHCID 27405863,3',5,5'-Tetrabromo-2,2'-bithiophene

생성물 1

HCID 8190873,3'-Dibromo-2,2'-bithiophene수율 91%

시약·촉매·용매 2

HCID 23994Zinc촉매HCID 176Acetic Acid용매

실험 절차

A mixture of 3,3′,5,5′-tetrabromo-2,2′-bithiophene (25 g, 52.3 mmol), ethanol (50 ml), water (50 ml) and glacial acetic acid (100 ml) was heated to reflux. Then the heating oil bath was removed, and zinc powder (13.1 g, 200 mmol) was added in portions at such a rate that the mixture continued to reflux. After the addition was complete, heating was continued, the mixture was refluxed for another 5 h and cooled down to room temperature. The unreacted zinc powder was filtered off and the filtrate was collected, diluted with diethyl ether and then washed twice with water. The ether solution was dried with anhydrous MgSO4 and the solvent was evaporated under reduced pressure. The crude product was recrystallized from hexane to afford a greenish crystal in the yield of 91% (15.3 g). 1H-NMR (CDCl3, ppm): δ7.40 (d, 2H, J=5 Hz), 7.11 (d, 2H, J=5 Hz).

후처리

  1. temperaturewas heated to reflux
  2. customThen the heating oil bath was removed
  3. temperatureto reflux
  4. additionAfter the addition
  5. temperatureheating
  6. temperaturethe mixture was refluxed for another 5 h
  7. filtrationThe unreacted zinc powder was filtered off
  8. customthe filtrate was collected
  9. additiondiluted with diethyl ether
  10. washwashed twice with water
  11. dry with materialThe ether solution was dried with anhydrous MgSO4
  12. customthe solvent was evaporated under reduced pressure
  13. customThe crude product was recrystallized from hexane
  14. customto afford a greenish crystal in the yield of 91% (15.3 g)

출처 및 근거

ORD 기록
ord-572205b302d64269a54f869ca2ee5641
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06361717B1

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