Potassium Carbonate → 2-(3-Bromo-5-methylphenoxy)-5-(trifluoromethyl)pyridine

HRID 1666452Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1666452
[Br:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[C:6]([CH3:8])[CH:7]=1.C([O-])([O-])=O.[K+].[K+].Cl[C:17]1[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][N:18]=1>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]=[C:6]([CH3:8])[CH:7]=1)[O:9][C:17]1[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][N:18]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 923422-Chloro-5-(trifluoromethyl)pyridineHCID 126484093-Bromo-5-methylphenol

Produkt 1

HCID 668769062-(3-Bromo-5-methylphenoxy)-5-(trifluoromethyl)pyridineAusbeute 85,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

To a solution of 3-bromo-5-methylphenol (2.0 g, 0.0106 mol) in DMF (15 mL) was added K2CO3 (2.93 g, 0.02 mol) at RT. 2-Chloro-5-(trifluoromethyl)pyridine (1.94 g, 0.0106 mol) was added and the reaction was refluxed at 110° C. for 12 h. The reaction mixture was quenched with water and extracted with EtOAc three times. The total organic extract was washed with water and brine, dried over sodium sulfate and concentrated under reduced pressure to give the title compound (3 g, 84.5%). 1H NMR (500 MHz, CDCl3): δ 8.45 (s, 1H), 7.92 (d, J=8.6 Hz, 1H), 7.26 (d, J=14.95 Hz, 1H), 7.13 (s, 1H), 7.03 (d, J=10 Hz, 1H), 6.90 (s, 1H), 2.36 (s, 3H).

Aufarbeitung

  1. customThe reaction mixture was quenched with water
  2. extractionextracted with EtOAc three times
  3. extractionThe total organic extract
  4. washwas washed with water and brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-026251bf2d3c480580b3d6a5c473e5ca
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08044052B2

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