Hydrochloric Acid → 2,6-dibromo-3-methyl-4-nitrophenol

HRID 1392551Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1392551
[CH3:1][C:2]1[CH:3]=[C:4]([OH:11])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].[Br-:12].[Br-:13].[Br-].C([N+](C)(C)C)C1C=CC=CC=1.C([N+](C)(C)C)C1C=CC=CC=1.C([N+](C)(C)C)C1C=CC=CC=1.C([O-])([O-])=O.[Ca+2].Cl>C(Cl)Cl.CO>[Br:12][C:3]1[C:2]([CH3:1])=[C:7]([N+:8]([O-:10])=[O:9])[CH:6]=[C:5]([Br:13])[C:4]=1[OH:11]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 10112Calcium CarbonateHCID 174123-Methyl-4-nitrophenolHCID 53442637Benzyltrimethylammoniumtribromide

Produkt 1

HCID 27696332,6-dibromo-3-methyl-4-nitrophenolAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
4 °C

Versuchsvorschrift

3-Methyl-4-nitrophenol (1.50 g, 9.75 mmol) was dissolved in a mixture of CH2Cl2 (30 mL) and methanol (30 mL) and cooled to 4° C. While stirring, benzyltrimethylammoniumtribromide (7.6 g, 19.5 mmol) and CaCO3 (1.95 g, 19.5 mmol) was added and the reaction was allowed to warm to room temperature. After 30 minutes, 1N HCl (45 mL) was added and reaction mixture left for 16 hours at 4° C. The organic phase was removed in vacuo and the resulting precipitate was collected by filtration and washed by water. The damp solid was co-evaporated with toluene and Et2O to yield 2.8 g (93%) of 2,6-dibromo-3-methyl-4-nitrophenol as a white solid.

Aufarbeitung

  1. temperatureto warm to room temperature
  2. customreaction mixture
  3. waitleft for 16 hours at 4° C
  4. customThe organic phase was removed in vacuo
  5. filtrationthe resulting precipitate was collected by filtration
  6. washwashed by water

Quellen und Nachweise

ORD-Eintrag
ord-0f6e2fab26c248aaa544b390801be90d
Quelldatensatz
uspto-grants-2008_03
Patentnummer
US07342127B2

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