Boron tribromide → 5-(4-methyl-5-(2-(trifluoromethyl)pyridin-3-yl)-4H-1,2,4-triazol-3-yl)-3-nitrobenzene-1,2-diol

HRID 42672Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 42672
C[O:2][C:3]1[CH:4]=[C:5]([C:14]2[N:15]([CH3:29])[C:16]([C:19]3[C:20]([C:25]([F:28])([F:27])[F:26])=[N:21][CH:22]=[CH:23][CH:24]=3)=[N:17][N:18]=2)[CH:6]=[C:7]([N+:11]([O-:13])=[O:12])[C:8]=1[O:9]C.B(Br)(Br)Br>ClCCl>[CH3:29][N:15]1[C:16]([C:19]2[C:20]([C:25]([F:27])([F:28])[F:26])=[N:21][CH:22]=[CH:23][CH:24]=2)=[N:17][N:18]=[C:14]1[C:5]1[CH:4]=[C:3]([OH:2])[C:8]([OH:9])=[C:7]([N+:11]([O-:13])=[O:12])[CH:6]=1

Komponenten

4

Edukt 2

HCID 25134Boron tribromideHCID 68702137HCID 68702137, Verbindung

Produkt 1

HCID 1363887205-(4-methyl-5-(2-(trifluoromethyl)pyridin-3-yl)-4H-1,2,4-triazol-3-yl)-3-nitrobenzene-1,2-diol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred suspension of 3-(5-(3,4-dimethoxy-5-nitrophenyl)-4-methyl-4H-1,2,4-triazol-3-yl)-2-(trifluoromethyl)pyridine (0.192 g, 0.47 mmol) in dichloromethane (20 mL) at −78° C. under argon was added boron tribromide (0.47 g, 1.88 mmol) dropwise. The resulting purple suspension was then allowed to stir at room temperature for seven hours before being cooled in an ice-water bath. The mixture was carefully quenched by the addition of methanol. After stirring at room temperature for thirty minutes, the volatiles were evaporated and the residue stirred with 2 N hydrochloric acid (5 mL) for thirty minutes. The resulting solid was filtered off, washed with water (25 mL) and then cold isopropanol (5 mL) to give, after drying, 5-(4-methyl-5-(2-(trifluoromethyl)pyridin-3-yl)-4H-1,2,4-triazol-3-yl)-3-nitrobenzene-1,2-diol was obtained as an orange solid, 0.154 g (86%).

Aufarbeitung

  1. temperaturebefore being cooled in an ice-water bath
  2. customThe mixture was carefully quenched by the addition of methanol
  3. stirringAfter stirring at room temperature for thirty minutes
  4. customthe volatiles were evaporated
  5. stirringthe residue stirred with 2 N hydrochloric acid (5 mL) for thirty minutes
  6. filtrationThe resulting solid was filtered off
  7. washwashed with water (25 mL)
  8. customcold isopropanol (5 mL) to give
  9. customafter drying

Quellen und Nachweise

ORD-Eintrag
ord-7685ee6cf3b54f9c89a3a5a13ed880f2
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536203B2

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