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Water → 2-fluoro-5H-dibenzo[a,d]cycloheptene

HRID 47221
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HRID 47221 반응식
[H-].[H-].[H-].[H-].[Li+].[Al+3].[Al+3].[Cl-].[Cl-].[Cl-].[F:11][C:12]1[CH:27]=[CH:26][C:15]2[C:16](=O)[C:17]3[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=3[CH:19]=[CH:20][C:14]=2[CH:13]=1.O>O1CCCC1.C(Cl)Cl>[F:11][C:12]1[CH:27]=[CH:26][C:15]2[CH2:16][C:17]3[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=3[CH:19]=[CH:20][C:14]=2[CH:13]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 962WaterHCID 6451240Aluminum(III) ChlorideHCID 14204212HCID 14204212, 화합물HCID 21226445Aluminium lithium hydride

생성물 1

HCID 227441622-fluoro-5H-dibenzo[a,d]cycloheptene수율 96%

시약·촉매·용매 2

HCID 6344Dichloromethane용매
HCID 8028Tetrahydrofuran용매2회

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온도
0 °C

실험 절차

LiAlH4 (0.0686 mol) was added dropwise to a suspension of AlCl3 (0.0718 mol) in tetrahydrofuran (75 ml), cooled on an ice-bath and under N2 atmosphere. The mixture was stirred for 10 minutes at 0° C. A solution of 2-fluoro-5H-dibenzo[a,d]cyclohepten-5-one (0.0653 mol and prepared as described in DE 3,644,462) in tetrahydrofuran (75 ml) was added dropwise and the resulting reaction mixture was allowed to warm to room temperature. Then, the reaction mixture was stirred and refluxed for 2 hours. The mixture was cooled on an ice-bath. Water and CH2Cl2 was added. The organic layer was washed with a saturated aqueous NaHCO3 solution, dried, filtered and the solvent was evaporated, yielding 13.16 g (96%) of 2-fluoro-5H-dibenzo[a,d]cycloheptene (intermediate 1)

후처리

  1. temperaturecooled on an ice-bath and under N2 atmosphere
  2. customthe resulting reaction mixture
  3. temperatureto warm to room temperature
  4. stirringThen, the reaction mixture was stirred
  5. temperaturerefluxed for 2 hours
  6. temperatureThe mixture was cooled on an ice-bath
  7. washThe organic layer was washed with a saturated aqueous NaHCO3 solution
  8. customdried
  9. filtrationfiltered
  10. customthe solvent was evaporated

출처 및 근거

ORD 기록
ord-2d7d19c670754520a27155e45e31aceb
출처 데이터셋
uspto-grants-2004_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06699858B2

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