Potassium Carbonate → 1-(2-Chloroethoxy)-4-chloro-3-nitrobenzene

HRID 399008

Reaktionsgleichung

Reaktionsgleichung von HRID 399008
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].C(=O)([O-])[O-].[K+].[K+].Br[CH:19]([Cl:21])[CH3:20]>CC(=O)CC>[Cl:21][CH2:19][CH2:20][O:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([N+:9]([O-:11])=[O:10])[CH:4]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 116541-Bromo-1-chloroethaneHCID 691274-Chloro-3-nitrophenol

Produkt 1

HCID 107761591-(2-Chloroethoxy)-4-chloro-3-nitrobenzene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6569Methyl Ethyl KetoneLösungsmittel

Versuchsvorschrift

To a 500 mL 3-neck round-bottom flask was added 4-chloro-3-nitro-phenol (10 g, 0.058 mol), potassium carbonate (20 g, 0.14 mol), bromochloroethane (34.5 g, 0.24 mol) and 2-butanone (200 mL). The mixture was mechanically stirred and heated to reflux for 20 hours under nitrogen then allowed to cool to room temperature and the solids were filtered. The solvent was evaporated under vacuum and the oil dissolved in diethyl ether (300 mL) and washed with 10% sodium hydroxide. The organic layer was dried over anhydrous magnesium sulfate, filtered and the solvent removed under vacuum. The product was dissolved in 1:1 methylene chloride-hexanes and filtered through a short pad silica. Upon concentration and standing 12.9 g (94.8.% %) of light yellow crystalline solid was afforded: mp 46°-48° C.; MS EI m/e 235, 237, 239 (M+); 1H NMR (400 MHz, DMSO-d6) δ 3.95 (t, 2H, J=5.2 Hz), 4.36 (t, 2H, J=5.2 Hz), 7.32 (dd, 1H, J=3.2, J=8.9 Hz), 7.66, (d, 1H, J=9 Hz), 7.69, (d, 1H, J=3.2 Hz).

Aufarbeitung

  1. temperatureheated
  2. temperatureto reflux for 20 hours under nitrogen
  3. filtrationthe solids were filtered
  4. customThe solvent was evaporated under vacuum
  5. dissolutionthe oil dissolved in diethyl ether (300 mL)
  6. washwashed with 10% sodium hydroxide
  7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customthe solvent removed under vacuum
  10. dissolutionThe product was dissolved in 1:1 methylene chloride-hexanes
  11. filtrationfiltered through a short pad silica
  12. concentrationUpon concentration
  13. customwas afforded

Quellen und Nachweise

ORD-Eintrag
ord-ff8f3147edac4eac8b8fc9ff5ea70257
Quelldatensatz
uspto-grants-1998_10
Patentnummer
US05817690

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