Toluene → 6-(5-Bromo-2-ethylphenyl)-2,2,4,4-tetramethylcyclohexane-1,3,5-trione

HRID 1470892ノート

反応式

HRID 1470892 の反応式
[CH3:1][C:2]1([CH3:13])[C:7](=[O:8])[C:6]([CH3:10])([CH3:9])[C:5](=[O:11])[CH2:4][C:3]1=[O:12].C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.[Br:26][C:27]1[CH:28]=[CH:29][C:30]([CH2:34][CH3:35])=[C:31]([Pb+3])[CH:32]=1.C(Cl)(Cl)Cl.C1(C)C=CC=CC=1>ClCCl.Cl>[Br:26][C:27]1[CH:32]=[CH:31][C:30]([CH2:34][CH3:35])=[C:29]([CH:4]2[C:3](=[O:12])[C:2]([CH3:13])([CH3:1])[C:7](=[O:8])[C:6]([CH3:9])([CH3:10])[C:5]2=[O:11])[CH:28]=1

参加物

7

反応物 4

HCID 1140TolueneHCID 6212ChloroformHCID 117691662,2,4,4-Tetramethylcyclohexane-1,3,5-trioneHCID 178476533HCID 178476533、化合物

生成物 1

HCID 684845366-(5-Bromo-2-ethylphenyl)-2,2,4,4-tetramethylcyclohexane-1,3,5-trione収率 63.9%

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
80 °C

実験手順

To a mixture of 2,2,4,4-tetramethylcyclohexane-1,3,5-trione (0.6 g, 3.6 mmol), 5-bromo-2-ethylphenyllead triacetate (2.27 g, 4.00 mmol) and N,N-dimethylaminopyridine (2.22 g, 18 mmol) is added anhydrous chloroform (25 ml) and toluene (6.3 ml), and the reaction mixture is heated at 80° C. for 3 hours. The mixture is diluted with dichloromethane (50 ml) and 2M aqueous hydrochloric acid (100 ml), and filtered through diatomaceous earth to remove inorganic residues. The filter cake is washed with dichloromethane, and all organic fractions are combined, washed with brine, dried over anhydrous magnesium sulphate then filtered. The filtrate is concentrated in vacuo and the residue is purified by flash column chromatography to give 6-(5-bromo-2-ethylphenyl)-2,2,4,4-tetramethylcyclohexane-1,3,5-trione as a white solid (0.84 g).

後処理

  1. filtrationfiltered through diatomaceous earth
  2. customto remove inorganic residues
  3. washThe filter cake is washed with dichloromethane
  4. washwashed with brine
  5. dry with materialdried over anhydrous magnesium sulphate
  6. filtrationthen filtered
  7. concentrationThe filtrate is concentrated in vacuo
  8. customthe residue is purified by flash column chromatography

出典と根拠

ORDレコード
ord-b3e6ef11c5cd4ef5b8aa3436970be577
出典データセット
uspto-grants-2015_04
特許番号
US09006429B2

反応ノート

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