1-(3,5-Dichlorophenyl)-2,2,2-trifluoroethan-1-one → 1-(4-Bromo-3-methylphenyl)-3-(3,5-dichlorophenyl)-4,4,4-trifluoro-2-buten-1-one

HRID 405693

반응식

HRID 405693 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:29])[CH:9]=P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:4][C:3]=1[CH3:30].[Cl:31][C:32]1[CH:33]=[C:34]([C:39](=O)[C:40]([F:43])([F:42])[F:41])[CH:35]=[C:36]([Cl:38])[CH:37]=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:29])[CH:9]=[C:39]([C:34]2[CH:35]=[C:36]([Cl:38])[CH:37]=[C:32]([Cl:31])[CH:33]=2)[C:40]([F:43])([F:42])[F:41])=[CH:4][C:3]=1[CH3:30]

참가 물질

4

반응물 2

HCID 27582311-(3,5-Dichlorophenyl)-2,2,2-trifluoroethan-1-oneHCID 866746711-(4-Bromo-3-methyl-phenyl)-2-(triphenylphosphanylidene)-ethanone

생성물 1

HCID 765635821-(4-Bromo-3-methylphenyl)-3-(3,5-dichlorophenyl)-4,4,4-trifluoro-2-buten-1-one수율 86.8%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

473 mg of 1-(4-Bromo-3-methyl-phenyl)-2-(triphenylphosphanylidene)-ethanone (Va) was refluxed with 243 mg of 1-(3,5-Dichloro-phenyl)-2,2,2-trifluoro-ethanone (VIa) (Journal of Physical Organic Chemistry (1989), 2(4), 363-6) in 3 ml of toluene for 3 hours. The solvent was then evaporated, and the residue was triturated with the mixture hexane:ethyl acetate 20:1. The solid that separated was filtered off and the filtrate after evaporation was purified on silica gel (40 g, hexane:acetate 10:1) giving 380 mg (86%) of 1-(4-Bromo-3-methyl-phenyl)-3-(3,5-dichloro-phenyl)-4,4,4-trifluoro-but-2-en-1-one (IVa) as a yellow oil which solidified on standing (mixture of E and Z isomers). 1H-NMR (CDCl3, δ in ppm): 2.41 (s) and 2.46 (s) (total of 3H), 6.80-7.80 (m, total of 7H).

후처리

  1. customThe solvent was then evaporated
  2. customthe residue was triturated with the mixture hexane:ethyl acetate 20:1
  3. customThe solid that separated
  4. filtrationwas filtered off
  5. customthe filtrate after evaporation
  6. customwas purified on silica gel (40 g, hexane:acetate 10:1)

출처 및 근거

ORD 기록
ord-ec7dc234e4c140b0aba05c481aeb5d25
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08754053B2

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