Dimethylformamide → 2-(4-Bromo-2-fluorophenyl)-2-methylpropanenitrile

HRID 1438249Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1438249
[H-].[Na+].[Br:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]#N)=[C:6]([F:13])[CH:5]=1.I[CH3:15].C[N:17]([CH:19]=O)C>C1COCC1.CCOC(C)=O>[Br:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]([CH3:15])([CH3:11])[C:19]#[N:17])=[C:6]([F:13])[CH:5]=1

Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 71723082-(4-Bromo-2-fluorophenyl)acetonitrile

Produkt 1

HCID 534036182-(4-Bromo-2-fluorophenyl)-2-methylpropanenitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a slurry of sodium hydride (60% dispersion in mineral oil, 0.82 g, 20.6 mmol) in DMF (20 mL) cooled to 0° C. was added a solution of (4-bromo-2-fluoro-phenyl)-acetonitrile (2.0 g, 9.35 mmol) from Step 1 above, dissolved in THF (10 mL). The reaction was stirred till gas evolution ceased, and then iodomethane (1.3 mL, 20.6 mmol) was added slowly. The reaction was stirred for 30 minutes, and then diluted with 100 mL EtOAc. The solids were removed by filtration, and the organic layer was washed with 100 mL water. The organic layer was dried over MgSO4, and then filtered. The mother liquor was concentrated by rotary evaporation, and the product was distilled under high vacuum (0.3 torr, 45° C.). Yield: 2.25 g, 99%. %. 1H NMR (CDCl3) δ: 2.81 (s, 3H), 2.88 (s, 3H), 7.20-7.25 (m, 3H).

Aufarbeitung

  1. stirringThe reaction was stirred for 30 minutes
  2. customThe solids were removed by filtration
  3. washthe organic layer was washed with 100 mL water
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationThe mother liquor was concentrated by rotary evaporation
  7. distillationthe product was distilled under high vacuum (0.3 torr, 45° C.)

Quellen und Nachweise

ORD-Eintrag
ord-a332514cd04c47be86e11e46b9dffb64
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07622605B2

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