N-bromobutanimide → 2,8-dimethyl-5H-dibenzo[a,d][7]annulen-5-one

HRID 1275901

반응식

HRID 1275901 반응식
[CH3:1][C:2]1[CH:18]=[CH:17][C:5]2[C:6](=[O:16])[C:7]3[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][C:8]=3[CH2:9][CH2:10][C:4]=2[CH:3]=1.BrN1C(=O)CCC1=O>C(OCC)(=O)C>[CH3:1][C:2]1[CH:18]=[CH:17][C:5]2[C:6](=[O:16])[C:7]3[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][C:8]=3[CH:9]=[CH:10][C:4]=2[CH:3]=1

참가 물질

4

반응물 2

HCID 67184N-bromobutanimideHCID 2211720110,11-dihydro-2,8-dimethyl-5H-dibenzo[a,d]cyclohepten-5-one

생성물 1

HCID 221172592,8-dimethyl-5H-dibenzo[a,d][7]annulen-5-one

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

반응 조건

온도
80 °C

실험 절차

10,11-Dihydro-2,8-dimethyl-5H-dibenzo[a,d]cyclohepten-5-one (European Patent, 1993, 0 25 589 322 A1) (6 g) and N-bromosuccinimide (5 g) in ethyl acetate (100 ml) was irradiated with a 500 W halogen lamp. After 5 hours the reaction mixture was cooled and quenched with brine. The organic layer was collected, dried (MgSO4) and evaporated under reduced pressure. The residue was dissolved in dry dimethylformamide, treated with 1,5-diazabicyclo[4.3.0]non-5-ene (3.5 ml) and heated at 80° C. for 0.25 hours. The cooled reaction mixture was washed with 2M HCl, brine, dried (MgSO4) and evaporated under reduced pressure. Purification was by chromatography eluting with toluene. Yield 4.5 g.

후처리

  1. temperatureAfter 5 hours the reaction mixture was cooled
  2. customquenched with brine
  3. customThe organic layer was collected
  4. dry with materialdried (MgSO4)
  5. customevaporated under reduced pressure
  6. dissolutionThe residue was dissolved in dry dimethylformamide
  7. additiontreated with 1,5-diazabicyclo[4.3.0]non-5-ene (3.5 ml)
  8. customThe cooled reaction mixture
  9. washwas washed with 2M HCl, brine
  10. dry with materialdried (MgSO4)
  11. customevaporated under reduced pressure
  12. customPurification
  13. washeluting with toluene

출처 및 근거

ORD 기록
ord-458b634a76da4bd4b11ba3c01f990cd4
출처 데이터셋
uspto-grants-2000_12
특허 번호
US06162808

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