Bromoacetonitrile → 2-(5-Bromo-4-fluoro-2-methylphenylamino)acetonitrile

HRID 2070817Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2070817
[CH3:1][CH2:2][N:3](C(C)C)C(C)C.[Br:10][C:11]1[C:12]([F:19])=[CH:13][C:14]([CH3:18])=[C:15]([CH:17]=1)[NH2:16].BrCC#N>C1COCC1>[Br:10][C:11]1[C:12]([F:19])=[CH:13][C:14]([CH3:18])=[C:15]([NH:16][CH2:1][C:2]#[N:3])[CH:17]=1

Komponenten

5

Edukt 3

HCID 11534BromoacetonitrileHCID 81531DiisopropylethylamineHCID 27827865-Bromo-4-fluoro-2-methylaniline

Produkt 1

HCID 866632582-(5-Bromo-4-fluoro-2-methylphenylamino)acetonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Hunig's Base (6.15 mL) was added to 5-bromo-4-fluoro-2-methylaniline (Example 318a, 3.59 g) in THF (50 mL) at room temperature followed by bromoacetonitrile (2.451 mL). The reaction was heated to reflux overnight. The reaction was cooled to room temperature and concentrated. 2N HCl and DCM were added. The organic layer was separated and dried (MgSO4) and concentrated to give the subtitle compound as a solid (6.61 g). 1H NMR δ (CDCl3) 6.92 (d, 1H), 6.80 (d, 1H), 4.13 (d, 2H), 3.78 (s, 1H), 2.13 (s, 3H).

Aufarbeitung

  1. temperatureThe reaction was heated
  2. temperatureto reflux overnight
  3. concentrationconcentrated
  4. addition2N HCl and DCM were added
  5. customThe organic layer was separated
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-987ec73f1c04419ea062310ef2dda255
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08299246B2

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