1,3-Difluoro-2-methoxy-4-nitrobenzene → 2,6-Difluoro-3-nitrophenol

HRID 243218Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 243218
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([F:11])[C:3]=1[O:12]C>Br.CC(O)=O.C1(C)C=CC=CC=1>[F:11][C:4]1[C:5]([N+:8]([O-:10])=[O:9])=[CH:6][CH:7]=[C:2]([F:1])[C:3]=1[OH:12]

Komponenten

5

Edukt 1

HCID 681577701,3-Difluoro-2-methoxy-4-nitrobenzene

Produkt 1

HCID 537967812,6-Difluoro-3-nitrophenol

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittelHCID 260Hydrogen BromideLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A solution of 1,3-difluoro-2-methoxy-4-nitrobenzene (0.50 g, 2.644 mmol) in 33% HBr in AcOH (4 mL) was heated at 100° C. for 1 h using microwave irradiation. The cooled reaction mixture was diluted with toluene and concentrated in vacuo. The resulting residue was partitioned between aqueous NaHCO3 and EtOAc. The aqueous phase was acidified with 1M HCl and extracted twice with DCM. The combined DCM extracts were washed with water, dried (Na2SO4) and concentrated in vacuo affording the title compound as a buff solid (0.29 g, 63%). 1H NMR (CDCl3, 300 MHz): 7.70 (1H, ddd, J=9.5, 7.8, 5.4 Hz), 7.06 (1H, ddd, J=9.4, 9.0, 2.2 Hz), 5.61 (1H, bs)

Aufarbeitung

  1. custommicrowave irradiation
  2. customThe cooled reaction mixture
  3. concentrationconcentrated in vacuo
  4. customThe resulting residue was partitioned between aqueous NaHCO3 and EtOAc
  5. extractionextracted twice with DCM
  6. washThe combined DCM extracts were washed with water
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-01b08e7178e64423bbd50f21c446c827
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08653089B2

Notizen zur Reaktion

Wird geladen…