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

HRID 1470892Notes

Reaction equation

[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

Participants

Conditions

Temperature: 80 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-b3e6ef11c5cd4ef5b8aa3436970be577
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09006429B2

Reaction notes

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