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

HRID 1470892노트

반응식

HRID 1470892 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 6344Dichloromethane용매

반응 조건

온도
80 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-b3e6ef11c5cd4ef5b8aa3436970be577
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09006429B2

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