Bromobenzene → 2-bromo-5,6,8,9-tetrahydro-5,5,9,9-tetramethyl-7H-benzocyclohepten-7-one

HRID 981802

반응식

HRID 981802 반응식
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:8][C:9](=[CH:11][C:12](=[O:17])[CH:13]=[C:14]([CH3:16])[CH3:15])[CH3:10].[Cl-].[Cl-].[Cl-].[Al+3]>C(=S)=S>[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[C:14]([CH3:16])([CH3:15])[CH2:13][C:12](=[O:17])[CH2:11][C:9]([CH3:10])([CH3:8])[C:4]=2[CH:3]=1

참가 물질

5

반응물 3

HCID 7961BromobenzeneHCID 10438PhoroneHCID 6451240Aluminum(III) Chloride

생성물 1

HCID 200710292-bromo-5,6,8,9-tetrahydro-5,5,9,9-tetramethyl-7H-benzocyclohepten-7-one

시약·촉매·용매 1

HCID 6348Carbon Disulfide용매

실험 절차

47.1 g of bromobenzene and 37.8 g of phorone are stirred at room temperature for 48 hours in the presence of 40 g of aluminum trichloride in 600 ml of carbon disulfide. The reaction mixture is then poured on to ice, extracted with diethyl ether. The extract is washed with water, dried and evaporated. After chromatography on silica gel with petroleum ether (low-boiling) and ethyl acetate (9:1) and recrystallization from hexane, there is obtained 2-bromo-5,6,8,9-tetrahydro-5,5,9,9-tetramethyl-7H-benzocyclohepten-7-one of m.p. 104°-105°.

후처리

  1. additionThe reaction mixture is then poured on to ice
  2. extractionextracted with diethyl ether
  3. washThe extract is washed with water
  4. customdried
  5. customevaporated
  6. customAfter chromatography on silica gel with petroleum ether (low-boiling) and ethyl acetate (9:1) and recrystallization from hexane

출처 및 근거

ORD 기록
ord-e0cd123ba4f94544bb7cbe6331cf05fa
출처 데이터셋
uspto-grants-1991_02
특허 번호
US04992574

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