Ethylene carbonate → 4-Bromo-2-(2-hydroxyethoxy)benzonitrile

HRID 60633

Reaktionsgleichung

Reaktionsgleichung von HRID 60633
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([OH:10])[CH:3]=1.C1(=O)O[CH2:14][CH2:13][O:12]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([O:10][CH2:14][CH2:13][OH:12])[CH:3]=1

Komponenten

5

Edukt 3

HCID 7303Ethylene carbonateHCID 11430Potassium CarbonateHCID 129669614-Bromo-2-hydroxybenzonitrile

Produkt 1

HCID 916363914-Bromo-2-(2-hydroxyethoxy)benzonitrileAusbeute 56,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
125 °C

Versuchsvorschrift

4-Bromo-2-hydroxybenzonitrile (1.00 g, 5.05 mmol), ethylene carbonate (467 mg, 5.30 mmol) and potassium carbonate (348 mg, 2.52 mmol) were suspended in DMF (2.00 mL) and heated to 125° C. for 4.5 h. The mixture was partitioned between EtOAc and water. The aqueous layer was then extracted with EtOAc (3×). The combined organic layers were washed with brine, dried (MgSO4), filtered and evaporated in vacuo. The residue was purified by FCC, using 0-100% EtOAc in cyclohexane to give the title compound (686 mg, 56%). 1H NMR (300 MHz, d4-MeOD): 3.92 (2H, t, J=4.7 Hz), 4.21 (2H, t, J=4.7 Hz), 7.26 (1H, dd, J=8.2, 1.7 Hz), 7.44 (1H, d, J=1.6 Hz), 7.53 (1H, d, J=8.2 Hz).

Aufarbeitung

  1. customThe mixture was partitioned between EtOAc and water
  2. extractionThe aqueous layer was then extracted with EtOAc (3×)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe residue was purified by FCC

Quellen und Nachweise

ORD-Eintrag
ord-ebb9091d56194fdf9e919b1eed26e7a9
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09440974B2

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