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

HRID 1470895노트

반응식

HRID 1470895 반응식
[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

참가 물질

7

반응물 3

HCID 1140TolueneHCID 156501652,2,6,6-Tetramethylthiopyran-3,5-dioneHCID 178476533HCID 178476533, 화합물

생성물 1

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

시약·촉매·용매 3

HCID 313Hydrochloric Acid용매HCID 6212Chloroform용매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-e812848443884fcf900638349d8468a6
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09006429B2

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