Bromobenzene → 1-Methoxy-3-phenoxybenzene

HRID 1416948

Reaktionsgleichung

Reaktionsgleichung von HRID 1416948
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1.Br[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C([O-])([O-])=O.[K+].[K+]>N1C=CC=CC=1.[Cu].S([O-])([O-])(=O)=O.[Cu+2]>[O:9]([C:5]1[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=[CH:7][CH:6]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Komponenten

7

Edukt 3

HCID 7961BromobenzeneHCID 90073-MethoxyphenolHCID 11430Potassium Carbonate

Produkt 1

HCID 742521-Methoxy-3-phenoxybenzeneAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23978CopperKatalysatorHCID 24462Copper SulfateKatalysatorHCID 1049PyridineLösungsmittel

Versuchsvorschrift

3-Methoxyphenol (287.4 g; 2.3 Mol), 316.0 g (2.0 Mol) of bromobenzene, 552 g (4.0 Mol) of K2CO3, 12.0 g (0.19 Mol) of activated copper (prepared according to Org. Syn. Coll. Vol. II, p 445-6), Cu(II) acetate hydrate 2.0 g (11 mMol), CuO powder (2.0 g; 25 mMol), and 2.0 g of copper sulfate (13 mMol) were combined in 1500 mL of dry pyridine. The resultant mixture was heated under reflux for 3 days. After cooling, the mixture was concentrated under reduced pressure, then treated with 6N HCl. Extraction was carried out with ether. The combined organics were washed with water, dilute NaOH, and water, then concentrated under reduced pressure. The residue was distilled in vacuo to give 3-phenoxyanisole, distilling at 138-40° C./2 mm pressure, 119 g (75% yield). H1NMR (CDCl3) d: 3.81 (s, 3 H), 6.61 (m, 2 H), 6.68 (d, J=7.8 Hz, 1 H), 7.06 (d, J=8.3, 2 H), 7.14 (t, J=7.4 Hz, 1 H), 7.25 (t, J=8.4 Hz, 1 H), 7.37 (t, J=7.8 Hz, 2 H).

Aufarbeitung

  1. temperatureunder reflux for 3 days
  2. temperatureAfter cooling
  3. concentrationthe mixture was concentrated under reduced pressure
  4. additiontreated with 6N HCl
  5. extractionExtraction
  6. washThe combined organics were washed with water, dilute NaOH, and water
  7. concentrationconcentrated under reduced pressure
  8. distillationThe residue was distilled in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-7e67478c7d044f8e9f64de0d01dde074
Quelldatensatz
uspto-grants-1999_06
Patentnummer
US05916922

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