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Water → HCID 58572624、化合物

HRID 1920806
ノート
印刷プレビュー

反応式

HRID 1920806 の反応式
[Br:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9](=[O:11])[CH3:10].[F:12][C:13]([F:21])(S(F)(=O)=O)C(O)=O.O>C(#N)C.[Cu]I>[Br:1][C:2]1[C:7]([O:8][CH:13]([F:21])[F:12])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9](=[O:11])[CH3:10]
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 962WaterHCID 27375162,2-Difluoro-2-(fluorosulfonyl)acetic acidHCID 232169621-(2-Bromo-3-hydroxyphenyl)ethanone

生成物 1

HCID 58572624HCID 58572624、化合物収率 18%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒
HCID 6342
Acetonitrile
溶媒
2 回

反応条件

温度
55 °C

実験手順

1-(2-Bromo-3-hydroxy phenyl)ethanone (6.50 g, 30.2 mmol), which had been obtained in Reference example 3 (3c), and copper (I) iodide (2.51 g, 13.2 mmol) were dissolved in acetonitrile (150 mL), followed by addition of a solution of difluoro(fluorosulfonyl)acetic acid (50.0 g, 281 mmol) dissolved in acetonitrile (50 mL) over 1 hour and 30 minutes under heating at 55° C. Upon the completion of the dropwise addition, the reaction solution was stirred at 55° C. for 3 hours, cooled to room temperature, added with water, and then extracted with ethyl acetate/hexane (2:1, V/V). The organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (neutral silica gel, hexane:ethyl acetate, 100:0-75:25, V/V and basic silica gel, hexane:ethyl acetate, 100:0-50:50, V/V) to give the title compound as a colorless oily substance (1.53 g, yield 18%).

後処理

  1. additionUpon the completion of the dropwise addition
  2. temperaturecooled to room temperature
  3. extractionextracted with ethyl acetate/hexane (2:1, V/V)
  4. washThe organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customThe residue was purified by silica gel chromatography (neutral silica gel, hexane:ethyl acetate, 100:0-75:25, V/V and basic silica gel, hexane:ethyl acetate, 100:0-50:50, V/V)

出典と根拠

ORDレコード
ord-8911c1723a774314b2a97a0102e2e9a9
出典データセット
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08173631B2

反応ノート

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