4-Bromo-2,5-difluoronitrobenzene → 5-Bromo-4-fluoro-2-nitrophenol

HRID 661076

Reaktionsgleichung

Reaktionsgleichung von HRID 661076
C[Si](C)(C)[O-:3].[Na+].[Br:7][C:8]1[C:13]([F:14])=[CH:12][C:11]([N+:15]([O-:17])=[O:16])=[C:10](F)[CH:9]=1>C1COCC1>[Br:7][C:8]1[C:13]([F:14])=[CH:12][C:11]([N+:15]([O-:17])=[O:16])=[C:10]([OH:3])[CH:9]=1

Komponenten

4

Edukt 2

HCID 27362864-Bromo-2,5-difluoronitrobenzeneHCID 23672319Sodium trimethylsilanolate

Produkt 1

HCID 576341145-Bromo-4-fluoro-2-nitrophenolAusbeute 205,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 2 M sodium trimethylsilanolate (15.6, 31.1 mmol) in THF was added dropwise to 4-bromo-2,5-difluoronitrobenzene (2.47 g, 10.4 mmol) under a nitrogen atmosphere. A bright red suspension was formed, and the mixture was refluxed for 27 hours. The mixture was cooled to room temperature and concentrated. Water (6 mL) was added, and the solution was acidified with a 10% HCl solution, extracted with DCM (70 mL×2). The organic layers were combined and concentrated to give 5-bromo-4-fluoro-2-nitrophenol (5.05 g, 2.06%). MS m/z: 236 (M+1). 1H NMR (400 MHz, CD3OD) δ ppm 7.48 (d, J=5.87 Hz, 1H), 7.95 (d, J=8.41 Hz, 1H).

Aufarbeitung

  1. customA bright red suspension was formed
  2. temperaturethe mixture was refluxed for 27 hours
  3. concentrationconcentrated
  4. additionWater (6 mL) was added
  5. extractionextracted with DCM (70 mL×2)
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-ed676f995b4443068691f4bacd65cbcc
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08084479B2

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