Sodium Cyanide → 2-(4-Bromo-2-fluorophenyl)acetonitrile

HRID 7704

Reaktionsgleichung

Reaktionsgleichung von HRID 7704
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]Br)=[C:4]([F:10])[CH:3]=1.[C-:11]#[N:12].[Na+]>CN(C=O)C>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][C:11]#[N:12])=[C:4]([F:10])[CH:3]=1

Komponenten

4

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a stirred solution of 4-bromo-2-fluoro benzyl bromide (1.5 g, 5.6 mmol) in DMF (50 mL) was added sodium cyanide (0.8 g, 16.8 mmol). The reaction was stirred at 90° C. for 1 h, and cooled at rt. After quenching with brine (50 mL) and diluted with EtOAc (100 mL), the EtOAc layer was washed with brine (50 mL), dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by flash chromatography (silica gel, hexanes:EtOAc 5:1) to afford 4-bromo-2-fluoro benzyl cyanide as yellow solid. MS (ESI) 307 (M+H)+.

Aufarbeitung

  1. temperaturecooled at rt
  2. customAfter quenching with brine (50 mL)
  3. additiondiluted with EtOAc (100 mL)
  4. washthe EtOAc layer was washed with brine (50 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash chromatography (silica gel, hexanes:EtOAc 5:1)

Quellen und Nachweise

ORD-Eintrag
ord-57e9aff840d84b2daacf95eb7f45676b
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07087601B2

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