1-Bromo-2-Chloroethane → HCID 22326897, Verbindung

HRID 1179239Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1179239
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:4]=1[OH:12].Br[CH2:14][CH2:15][Cl:16].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:16][CH2:15][CH2:14][O:12][C:4]1[CH:5]=[CH:6][C:7]([N+:9]([O-:11])=[O:10])=[CH:8][C:3]=1[O:2][CH3:1]

Komponenten

5

Edukt 3

HCID 78491-Bromo-2-ChloroethaneHCID 11430Potassium CarbonateHCID 767382-Methoxy-4-nitrophenol

Produkt 1

HCID 22326897HCID 22326897, VerbindungAusbeute 56,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A mixture of 2-methoxy-4-nitro-phenol (2.50 g, 14.8 mmol), 1-bromo-2-chloro-ethane (1.35 mL, 16.3 mmol) and potassium carbonate (4.08 g, 29.6 mmol) in DMF (50 mL) in a sealed tube was heated at 90° C. for 18 h. The reaction was cooled and filtered, washing with ethyl acetate. The filtrate was washed with sodium bicarbonate, water (4 times) and brine, was dried (sodium sulfate) and evaporated. Purification by flash chromatography (SiO2) eluted with 35:65 ethyl acetate:hexanes provided 1-(2-chloro-ethoxy)-2-methoxy-4-nitro-benzene (1.93 g, 56% yield) as an off-white solid. 1H-NMR (DMSO-d6, 500 MHz) 7.89 (dd, 1H), 7.76 (d, 1H), 7.21 (d, 1H), 4.41 (t, 2H), 4.00 (t, 2H), 3.90 (s, 3H) ppm; HPLC (Method A) 3.781 min.

Aufarbeitung

  1. temperatureThe reaction was cooled
  2. filtrationfiltered
  3. washwashing with ethyl acetate
  4. washThe filtrate was washed with sodium bicarbonate, water (4 times) and brine
  5. dry with materialwas dried (sodium sulfate)
  6. customevaporated
  7. customPurification by flash chromatography (SiO2)
  8. washeluted with 35:65 ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-4c354cb50ad748608a6bab6e2739fac5
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07279469B2

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