Sodium Cyanide → 2-(4-Bromo-2,3-difluorophenyl)acetonitrile

HRID 576178Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 576178
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]Br)=[C:4]([F:10])[C:3]=1[F:11].[C-:12]#[N:13].[Na+]>C(O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:12]#[N:13])=[C:4]([F:10])[C:3]=1[F:11]

Komponenten

4

Edukt 2

HCID 8929Sodium CyanideHCID 696728541-Bromo-4-(bromomethyl)-2,3-difluorobenzene

Produkt 1

HCID 904160312-(4-Bromo-2,3-difluorophenyl)acetonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
10 °C

Versuchsvorschrift

To a solution of 1-bromo-4-(bromomethyl)-2,3-difluorobenzene (330 mg, 1.154 mmol) in ethanol (10 mL) stirred under N2 at 0° C. was added NaCN (73.5 mg, 1.500 mmol) in one charge. The reaction mixture was stirred at 10° C. for 12 h. Then the solution was concentrated and distributed between EA and saturated NaHCO3 solution. The combined organic extract was washed with brine, dried over MgSO4, filtered and concentrated. The resulting 2-(4-bromo-2,3-difluorophenyl)acetonitrile was used in the next step without further purification. TLC (PE/EA=5:1, Rf 0.6): 1H NMR (400 MHz, CDCl3) δ 7.39 (ddd, J=1.8, 6.1, 8.2 Hz, 1H), 7.15 (t, J=6.8 Hz, 1H), 3.78 (s, 2H).

Aufarbeitung

  1. additioncharge
  2. concentrationThen the solution was concentrated
  3. extractionThe combined organic extract
  4. washwas washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting 2-(4-bromo-2,3-difluorophenyl)acetonitrile was used in the next step without further purification

Quellen und Nachweise

ORD-Eintrag
ord-e390042f262e4894bb53643661eafb6a
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09035063B2

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