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Toluene → 2-(3,5-Dichlorophenyl)-3,3,3-trifluoroprop-1-en-1-yl phenyl sulfone

HRID 62627
ノート
印刷プレビュー

反応式

HRID 62627 の反応式
[Cl-].[Mg+2].[Cl-].[CH3:4][S:5]([CH2:8]P(=O)(OCC)OCC)(=[O:7])=[O:6].C(N(CC)CC)C.[Cl:24][C:25]1[CH:26]=[C:27]([C:32](=O)[C:33]([F:36])([F:35])[F:34])[CH:28]=[C:29]([Cl:31])[CH:30]=1.[C:38]1(C)[CH:43]=[CH:42]C=[CH:40][CH:39]=1>O.C(#N)C>[C:4]1([S:5]([CH:8]=[C:32]([C:27]2[CH:26]=[C:25]([Cl:24])[CH:30]=[C:29]([Cl:31])[CH:28]=2)[C:33]([F:36])([F:35])[F:34])(=[O:6])=[O:7])[CH:42]=[CH:43][CH:38]=[CH:39][CH:40]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

HCID 1140TolueneHCID 8471TriethylamineHCID 533797Diethyl (methanesulfonylmethyl)phosphonateHCID 27582311-(3,5-Dichlorophenyl)-2,2,2-trifluoroethan-1-oneHCID 5360315Magnesium Chloride2 回

生成物 1

HCID 1239447962-(3,5-Dichlorophenyl)-3,3,3-trifluoroprop-1-en-1-yl phenyl sulfone
収率 78%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6342Acetonitrile溶媒

実験手順

Magnesium chloride (dry, 241 mg, 2.53 mmol) was put in a flask under a nitrogen atmosphere and acetonitrile (3.5 mL) was added. The mixture was stirred for five minutes at room temperature. Diethyl [(methylsulfonyl)methyl]phosphonate (500 mg, 2.17 mmol) was added. After 10 minutes stirring the magnesium chloride was nearly dissolved. Triethylamine (378 μL, 2.72 mmol) was added and after 10 minutes at room temperature a slightly orange solution was obtained. Then 1-(3,5-dichlorophenyl)-2,2,2-trifluoroethanone (468 mg, 94% purity, 1.81 mmol) was added. After thirty minutes water (10 mL) and toluene (10 mL) were added and the phases were separated. After extracting the aqueous phase with toluene (10 mL) the combined organic phases were dried over sodium sulfate, filtered and the solvents evaporated. 2-(3,5-dichlorophenyl)-3,3,3-trifluoroprop-1-en-1-yl phenyl sulfone was obtained (540 g, >98% purity, 78% yield, E/Z (not assigned)=56/44).

後処理

  1. dissolutionwas nearly dissolved
  2. customwas obtained
  3. customthe phases were separated
  4. extractionAfter extracting the aqueous phase with toluene (10 mL) the combined organic phases
  5. dry with materialwere dried over sodium sulfate
  6. filtrationfiltered
  7. customthe solvents evaporated

出典と根拠

ORDレコード
ord-bfcc33f41f1d4b3db3e43b3b48b9f391
出典データセット
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09447036B2

反応ノート

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