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Water → HCID 58572624, Verbindung

HRID 1920806
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1920806
[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]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 962WaterHCID 27375162,2-Difluoro-2-(fluorosulfonyl)acetic acidHCID 232169621-(2-Bromo-3-hydroxyphenyl)ethanone

Produkt 1

HCID 58572624HCID 58572624, VerbindungAusbeute 18 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Katalysator
HCID 6342AcetonitrileLösungsmittel2×

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

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%).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-8911c1723a774314b2a97a0102e2e9a9
Quelldatensatz
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08173631B2

Notizen zur Reaktion

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