Toluene → Methyl 4-(5-cyano-7-isopropenyl-1,3-benzoxazol-2-yl)benzoate

HRID 2066829Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2066829
Br[C:2]1[C:10]2[O:9][C:8]([C:11]3[CH:19]=[CH:18][C:14]([C:15]([O-:17])=[O:16])=[CH:13][CH:12]=3)=[N:7][C:6]=2[CH:5]=[C:4]([C:20]#[N:21])[CH:3]=1.[C:22]1(C)[CH:27]=CC=C[CH:23]=1.[C:29](=O)([O-])[O-].[Na+].[Na+].C(B(O)O)=CC(=C)C>C(O)C.O>[C:20]([C:4]1[CH:3]=[C:2]([C:22]([CH3:27])=[CH2:23])[C:10]2[O:9][C:8]([C:11]3[CH:19]=[CH:18][C:14]([C:15]([O:17][CH3:29])=[O:16])=[CH:13][CH:12]=3)=[N:7][C:6]=2[CH:5]=1)#[N:21]

Komponenten

7

Edukt 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 74788214HCID 74788214, Verbindung2×HCID 86643502HCID 86643502, Verbindung2×

Produkt 1

HCID 68409145Methyl 4-(5-cyano-7-isopropenyl-1,3-benzoxazol-2-yl)benzoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
91 °C

Versuchsvorschrift

To a 5-l, 3-neck round-bottom flask fitted with a stirring paddle, a condenser blanketed with nitrogen, and a thermocouple, was added 4-(7-bromo-5-cyano-1,3-benzoxazol-2-yl)benzoate (55.5 g, INTERMEDIATE 35), toluene (2 l), water (375 ml), ethanol (150 ml), 2M aqueous sodium carbonate (250 ml), and isoprenylboronic acid (83.4 g, INTERMEDIATE 37). The mixture was purged with nitrogen three times and then tetrakis(triphenylphosphine)palladium(0) (9.1 g) was added, and the mixture was purged three times with nitrogen. The mixture was heated to reflux (91° C.) and stirred at this temperature overnight. The mixture was then cooled to 20° C. and the product was filtered, washed with water, dried, and transferred to a 3-l round-bottom flask and rinsed with toluene (1 l). Residual solvent was removed in vacuo. Mass spectrum (ESI) 319.1 (M+1).

Aufarbeitung

  1. customThe mixture was purged with nitrogen three times
  2. additiontetrakis(triphenylphosphine)palladium(0) (9.1 g) was added
  3. customthe mixture was purged three times with nitrogen
  4. temperatureThe mixture was heated
  5. temperatureThe mixture was then cooled to 20° C.
  6. filtrationthe product was filtered
  7. washwashed with water
  8. customdried
  9. customtransferred to a 3-l round-bottom flask
  10. washrinsed with toluene (1 l)
  11. customResidual solvent was removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-5ed79b36660d488d9baa241091216cb2
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08293721B2

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