Water → 2-(4-Fluoronaphthalen-1-yl)acetonitrile

HRID 8212Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 8212
Cl[CH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([F:13])=[CH:5][CH:4]=1.[C-:14]#[N:15].[Na+].O>CN(C)C=O>[F:13][C:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]([CH2:2][C:14]#[N:15])=[CH:4][CH:5]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 8929Sodium CyanideHCID 156574171-(Chloromethyl)-4-fluoronaphthalene

Produkt 1

HCID 219925322-(4-Fluoronaphthalen-1-yl)acetonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A solution of 1-chloromethyl-4-fluoronaphthalene (5.45 g, 5.66 mmol), sodium cyanide (333 mg, 6.79 mmol), and water (2 mL) in N,N-dimethylformamide (30 mL) is stirred for 8 h, then heated at 70° C. for 15 h. The mixture is cooled to room temperature and partitioned between saturated sodium bicarbonate solution and ethyl acetate. The organic portion is washed with three portions of water, one portion of brine, dried (sodium sulfate), filtered and evaporated. The residue is chromatographed on SiO2 (30% ethyl acetate/hexane) to yield the title compound, 4.67 g (90%), as a light brown solid. 1H NMR (CDCl3): δ 8.19 (d, J=8 Hz, 1H), 7.87 (d, J=8 Hz, 1H), 7.68 (ddd, J=8, 7, 1 Hz, 1H), 7.63 (ddd, J=8, 7, 1 Hz, 1H), 7.51 (dd, J=8, 5 Hz, 1H), 7.14 (dd, J=10, 8 Hz, 1H), 4.09 (s, 2H).

Aufarbeitung

  1. temperatureThe mixture is cooled to room temperature
  2. custompartitioned between saturated sodium bicarbonate solution and ethyl acetate
  3. washThe organic portion is washed with three portions of water, one portion of brine
  4. dry with materialdried (sodium sulfate)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue is chromatographed on SiO2 (30% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-fd8e422ad9204a379e007b50fb4602f2
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07087626B2

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