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

HRID 555390Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 555390
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 recrystallized 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. customrecrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-6819d368475344b7b7504e5e49d13ab9
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08053450B2

Notizen zur Reaktion

Wird geladen…