Hydrochloric Acid → 3-[(2,3-Difluoro-6-nitrophenyl)oxy]-5-(methyloxy)benzonitrile

HRID 1875240Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1875240
[H-].[Na+].[OH:3][C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([O:12][CH3:13])[CH:11]=1)[C:7]#[N:8].[F:14][C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[C:17](F)[C:16]=1[F:25].Cl>C1COCC1>[F:25][C:16]1[C:15]([F:14])=[CH:20][CH:19]=[C:18]([N+:21]([O-:23])=[O:22])[C:17]=1[O:3][C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([O:12][CH3:13])[CH:11]=1)[C:7]#[N:8]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 698711,2,3-Trifluoro-4-nitrobenzeneHCID 229962023-Hydroxy-5-methoxybenzonitrile

Produkt 1

HCID 687222673-[(2,3-Difluoro-6-nitrophenyl)oxy]-5-(methyloxy)benzonitrileAusbeute 92,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

NaH (2.05 g, 51.2 mmol) was added portionwise to a 0° C. solution of 3-hydroxy-5-(methyloxy)benzonitrile (7.63 g, 51.2 mmol) (prepared following the procedure in Magano et al. J. Org. Chem. 2006, 71, 7103) in THF (205 ml). When addition was complete, the thick suspension was stirred at this temperature for another 30 mins, and trifluoronitrobenzene (9.51 g, 53.7 mmol) was then added. The reaction mixture was stirred at RT for 3 h, dilute HCl was added and the solution was extracted with EtOAc. The organic layer was dried (Na2SO4), filtered, evaporated and purified by silica gel chromatography (0-30% EtOAc/hexanes) to afford the title compound (14.44 g, 92%) as a light yellow solid. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.96 (ddd, J=9.36, 4.97, 2.24 Hz, 1H) 7.28-7.35 (m, 1H) 6.95 (d, J=0.73 Hz, 1H) 6.78 (t, J=2.15 Hz, 1H) 6.73 (s, 1H) 3.85 (s, 3H).

Aufarbeitung

  1. customprepared
  2. additionWhen addition
  3. stirringThe reaction mixture was stirred at RT for 3 h
  4. extractionthe solution was extracted with EtOAc
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated
  8. custompurified by silica gel chromatography (0-30% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-73620ff5ede249ffaffdcb6c45f97147
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08304419B2

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