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

HRID 339471
ノート
印刷プレビュー

反応式

HRID 339471 の反応式
[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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 2734996copper(II) trifluoromethanesulfonate触媒
HCID 1140
Toluene
溶媒

反応条件

温度
160 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-af09a8cffd5a4e75982d29490f4cbe5b
出典データセット
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08895474B2

反応ノート

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