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Water → (3-Bromophenyl)acetonitrile

HRID 2243211
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2243211
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([NH2:11])=O)[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.FC(F)(F)C(OC(=O)C(F)(F)F)=O.O>O1CCOCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]#[N:11])[CH:5]=[CH:6][CH:7]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 117360272-(3-Bromophenyl)acetamide

Produkt 1

HCID 36023(3-Bromophenyl)acetonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

2-(3-Bromophenyl)acetamide (10.0 g, 46.73 mmol) (example 1) in dry 1,4-dioxane (100 mL) was cooled to 0° C. Triethylamine (18.91 g, 187.92 mmol) was added and the reaction mixture was stirred for about 10 minutes. Trifluoroacetic anhydride (39.26 g, 186.92 mmol) was added dropwise at 0° C. and the reaction mixture was stirred at room temperature for about 12 hours. The reaction mixture was poured into cold water, extracted with ethyl acetate, washed with water, dried over anhydrous sodium sulphate, filtered and the solvent evaporated under vacuum. An oily residue was obtained which was purified by column chromatography over silica gel using ethyl acetate and hexane (1:49) to afford the title compound as light yellow colored oil. Yield: 8.4 g.

Aufarbeitung

  1. stirringthe reaction mixture was stirred at room temperature for about 12 hours
  2. extractionextracted with ethyl acetate
  3. washwashed with water
  4. dry with materialdried over anhydrous sodium sulphate
  5. filtrationfiltered
  6. customthe solvent evaporated under vacuum
  7. customAn oily residue was obtained which
  8. customwas purified by column chromatography over silica gel

Quellen und Nachweise

ORD-Eintrag
ord-7d933871668142a38797fe91a2d5d3aa
Quelldatensatz
uspto-grants-2010_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07674811B2

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