2-Tert-Butylphenol → Pyridine, 2-[2-(1,1-dimethylethyl)phenoxy]-3-nitro-

HRID 2377802Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2377802
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[C:11]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[OH:21])([CH3:14])([CH3:13])[CH3:12].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.O>[C:11]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[O:21][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1)([CH3:14])([CH3:12])[CH3:13]

Komponenten

6

Edukt 3

HCID 69232-Tert-ButylphenolHCID 10796Cesium carbonateHCID 796132-Chloro-3-nitropyridine

Produkt 1

HCID 59857513Pyridine, 2-[2-(1,1-dimethylethyl)phenoxy]-3-nitro-Ausbeute 90,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A solution of 2-chloro-3-nitropyridine (21.05 g, 132.7 mmol) in DMF (100 mL) was treated with 2-tert-butylphenol (23.5 mL, 152.6 mmol) and cesium carbonate (129.8 g, 398.3 mmol). The mixture was heated at 80° C. for 30 h. The reaction was cooled to rt, and the mixture was poured in water (1 L) with stirring. The yellow precipitate formed was filtered and washed with water, and recrystalized from ethanol to afford 1a as beige crystals (32.83 g, 90%). 1H NMR (400 MHz, CD3OD) δ ppm 1.34 (s, 9H), 6.93 (m, 1H), 7.22 (m, 3H), 7.47 (m, 1H), 8.31 (dd, J=4.82, 1.75 Hz, 1H), 8.46 (dd, J=7.89, 1.75 Hz, 1H).

Aufarbeitung

  1. temperatureThe reaction was cooled to rt
  2. customThe yellow precipitate formed
  3. filtrationwas filtered
  4. washwashed with water
  5. customrecrystalized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-034277255714455d9b3dc837368a1c13
Quelldatensatz
uspto-grants-2008_12
Patentnummer
US07470712B2

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