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1,3-Dibromo-5,5-dimethylhydantoin → 3'-Bromo-2,2,2-trifluoro-5'-(trifluoromethyl)acetophenone

HRID 551340
ノート
印刷プレビュー

反応式

HRID 551340 の反応式
[F:1][C:2]([F:16])([F:15])[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([F:14])([F:13])[F:12])[CH:6]=1)=[O:4].[Br:17]N1C(C)(C)C(=O)N(Br)C1=O>C(O)(=O)C.S(=O)(=O)(O)O>[Br:17][C:9]1[CH:10]=[C:5]([C:3](=[O:4])[C:2]([F:15])([F:16])[F:1])[CH:6]=[C:7]([C:11]([F:12])([F:13])[F:14])[CH:8]=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

5

反応物 2

HCID 64791,3-Dibromo-5,5-dimethylhydantoinHCID 1365592,2,2-Trifluoro-3'-(trifluoromethyl)acetophenone

生成物 1

HCID 716518093'-Bromo-2,2,2-trifluoro-5'-(trifluoromethyl)acetophenone収率 163.5%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 1118Sulfuric Acid溶媒

反応条件

温度
35 °C

実験手順

To a stirred solution of 2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethanone (5.00 g) in glacial acetic acid (1.0 mL) and concentrated sulfuric acid (6.0 mL) at 0° C. was added 1,3-dibromo-5,5-dimethylhydantoin (3.54 g). After stirring at 35° C. for 3.5 hours, the reaction mixture was poured into ice-water (60 mL) and extracted with chloroform (30 mL×2). The organic extracts were combined, washed with saturated aqueous sodium hydrogencarbonate solution (50 mL×1) and brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was dissolved in hexane (20 mL) and filtered, and the filtrate was concentrated under reduced pressure to provide the title compound as a yellow oil (6.50 g).

後処理

  1. extractionextracted with chloroform (30 mL×2)
  2. washwashed with saturated aqueous sodium hydrogencarbonate solution (50 mL×1) and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe resulting residue was dissolved in hexane (20 mL)
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-720099d317f14a0dad551777dfd28d07
出典データセット
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07947715B2

反応ノート

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