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

HRID 981802

反応式

HRID 981802 の反応式
[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

参加物

5

反応物 3

HCID 7961BromobenzeneHCID 10438PhoroneHCID 6451240Aluminum(III) Chloride

生成物 1

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

試薬・触媒・溶媒 1

HCID 6348Carbon Disulfide溶媒

実験手順

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°.

後処理

  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

出典と根拠

ORDレコード
ord-e0cd123ba4f94544bb7cbe6331cf05fa
出典データセット
uspto-grants-1991_02
特許番号
US04992574

関連ノート

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