Toluene → 4-(5-Bromo-2-ethylphenyl)-2,2,6,6-tetramethylthiopyran-3,5-dione

HRID 1470895ノート

反応式

HRID 1470895 の反応式
[CH3:1][C:2]1([CH3:12])[C:7](=[O:8])[CH2:6][C:5](=[O:9])[C:4]([CH3:11])([CH3:10])[S:3]1.C1(C)C=CC=CC=1.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.[Br:32][C:33]1[CH:34]=[CH:35][C:36]([CH2:40][CH3:41])=[C:37]([Pb+3])[CH:38]=1>C(Cl)(Cl)Cl.ClCCl.Cl>[Br:32][C:33]1[CH:38]=[CH:37][C:36]([CH2:40][CH3:41])=[C:35]([CH:6]2[C:7](=[O:8])[C:2]([CH3:12])([CH3:1])[S:3][C:4]([CH3:11])([CH3:10])[C:5]2=[O:9])[CH:34]=1

参加物

7

反応物 3

HCID 1140TolueneHCID 156501652,2,6,6-Tetramethylthiopyran-3,5-dioneHCID 178476533HCID 178476533、化合物

生成物 1

HCID 684876664-(5-Bromo-2-ethylphenyl)-2,2,6,6-tetramethylthiopyran-3,5-dione

試薬・触媒・溶媒 3

HCID 313Hydrochloric Acid溶媒HCID 6212Chloroform溶媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of 2,2,6,6-tetramethylthiopyran-3,5-dione (prepared according to the procedure of E. Er and P. Margaretha, Helvetica Chimica Acta (1992), 75(7), 2265-69) (1.8 g, 9.9 mmol) and N,N-dimethylaminopyridine (5.3 g, 4.34 mmol) in chloroform (60 ml), is added toluene (18 ml) then 5-bromo-2-ethylphenyllead triacetate (6.2 g, 1.09 mmol) in one portion. The resulting mixture is heated at reflux for 2 hours, then allowed to cool to ambient temperature, diluted with dichloromethane and 1M aqueous hydrochloric acid, and the organic phase is separated. The organic phase is concentrated under reduced pressure, and the residue is purified by flash chromatography on silica gel (hexane/ethyl acetate 95:5 to 7:3 ratio), giving 4-(5-bromo-2-ethylphenyl)-2,2,6,6-tetramethylthiopyran-3,5-dione (2.42 g) as an orange solid.

後処理

  1. temperatureThe resulting mixture is heated
  2. temperatureat reflux for 2 hours
  3. customthe organic phase is separated
  4. concentrationThe organic phase is concentrated under reduced pressure
  5. customthe residue is purified by flash chromatography on silica gel (hexane/ethyl acetate 95:5 to 7:3 ratio)

出典と根拠

ORDレコード
ord-e812848443884fcf900638349d8468a6
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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