Phenyltrimethylammonium bromide dibromide → 1-(Benzo[b]thiophen-7-yl)-2-bromopropan-1-one

HRID 2183655

반응식

HRID 2183655 반응식
[Br-:1].[Br-].[Br-].C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.[S:34]1[CH:38]=[CH:37][C:36]2[CH:39]=[CH:40][CH:41]=[C:42]([C:43](=[O:46])[CH2:44][CH3:45])[C:35]1=2>O1CCCC1>[S:34]1[CH:38]=[CH:37][C:36]2[CH:39]=[CH:40][CH:41]=[C:42]([C:43](=[O:46])[CH:44]([Br:1])[CH3:45])[C:35]1=2

참가 물질

4

반응물 2

HCID 17977687Phenyltrimethylammonium bromide dibromide3회HCID 224738971-(Benzo[b]thiophen-7-yl)propan-1-one

생성물 1

HCID 224741431-(Benzo[b]thiophen-7-yl)-2-bromopropan-1-one수율 112.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Phenyltrimethylammonium tribromide (1.52 g) was added in portions under nitrogen at 0° C. over 30 minutes to a stirred solution of 1-(benzo[b]thiophen-7-yl)propan-1-one (0.77 g) in tetrahydrofuran (110 ml), then the mixture was stirred at ambient temperature for 18 hours. Further phenyltrimethylammonium tribromide (0.76 g) was added and the mixture was heated under reflux for 4 hours. Further phenyltrimethylammonium tribromide (0.76 g) was added, then the mixture was heated under reflux for 90 minutes, cooled to ambient temperature and filtered. The solvent was removed in vacuo and the residue was purified by flash chromatography over silica using a 7:3 mixture of petroleum ether (b.p. 60-80° C.) and dichloromethane as eluant. Appropriate fractions were combined and the solvents removed in vacuo to give 1-(benzo[b]thiophen-7-yl)-2-bromopropan-1-one (0.71 g) as an oil which was used without further purification.

후처리

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 4 hours
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for 90 minutes
  5. temperaturecooled to ambient temperature
  6. filtrationfiltered
  7. customThe solvent was removed in vacuo
  8. customthe residue was purified by flash chromatography over silica using
  9. additiona 7:3 mixture of petroleum ether (b.p. 60-80° C.) and dichloromethane as eluant
  10. customthe solvents removed in vacuo

출처 및 근거

ORD 기록
ord-8f8daf008bb5407a9b9d5c9062fb3418
출처 데이터셋
uspto-grants-2005_05
특허 번호
US06900216B2

연결된 노트

불러오는 중…