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4-Chlorophenol → 2-[5-(4-Chlorophenoxy)-2-trifluoromethoxyphenyl]cyclopentane-1,3-dione

HRID 339471
노트
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HRID 339471 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[C:16]1[CH:17]=[CH:18][C:19]([O:29][C:30]([F:33])([F:32])[F:31])=[C:20]([CH:22]2[C:26](=[O:27])[CH2:25][CH2:24][C:23]2=[O:28])[CH:21]=1>C1(C)C=CC=CC=1.[O-]S(C(F)(F)F)(=O)=O.[Cu+2].[O-]S(C(F)(F)F)(=O)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:16]2[CH:17]=[CH:18][C:19]([O:29][C:30]([F:31])([F:32])[F:33])=[C:20]([CH:22]3[C:26](=[O:27])[CH2:25][CH2:24][C:23]3=[O:28])[CH:21]=2)=[CH:4][CH:3]=1
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참가 물질

6

반응물 3

HCID 46844-ChlorophenolHCID 10796Cesium carbonateHCID 666778042-(5-Bromo-2-trifluoromethoxyphenyl)cyclopentane-1,3-dione

생성물 1

HCID 666779502-[5-(4-Chlorophenoxy)-2-trifluoromethoxyphenyl]cyclopentane-1,3-dione

시약·촉매·용매 2

HCID 2734996copper(II) trifluoromethanesulfonate촉매
HCID 1140
Toluene
용매

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온도
160 °C

실험 절차

To a mixture of 4-chlorophenol (0.473 g, 3.69 mmol), cesium carbonate (0.521 g, 1.48 mmol), copper triflate (0.013 g, 0.04 mmol) and powdered 5 Å molecular sieves (0.400 g) is added a solution of 2-(5-bromo-2-trifluoromethoxyphenyl)cyclopentane-1,3-dione (0.249 g, 0.74 mmol) in anhydrous toluene (3.5 ml). The mixture is flushed with nitrogen and heated at 160° C. for 1 hour under microwave radiation, then for a further 1 h at 170° C. After cooling to room temperature the crude product is partitioned between dichloromethane (5 ml) and 2M hydrochloric acid (5 ml), and the organic phase is separated then concentrated in vacuo. The residue is then purified by flash column chromatography on silica gel (ethyl acetate/iso-hexane eluant) to afford 2-[5-(4-chlorophenoxy)-2-trifluoromethoxyphenyl]cyclopentane-1,3-dione as a white solid.

후처리

  1. customThe mixture is flushed with nitrogen
  2. temperatureAfter cooling to room temperature the crude product
  3. customis partitioned between dichloromethane (5 ml) and 2M hydrochloric acid (5 ml)
  4. customthe organic phase is separated
  5. concentrationthen concentrated in vacuo
  6. customThe residue is then purified by flash column chromatography on silica gel (ethyl acetate/iso-hexane eluant)

출처 및 근거

ORD 기록
ord-af09a8cffd5a4e75982d29490f4cbe5b
출처 데이터셋
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08895474B2

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