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

HRID 2093582Notes

Reaction equation

HRID 2093582 reaction equation
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]

Participants

7

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 74788214HCID 74788214, compound2×HCID 86643502HCID 86643502, compound2×

Product 1

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

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
91 °C

Procedure

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 1) toluene (2 l), water (375 ml), ethanol (150 ml), 2M aqueous sodium carbonate (250 ml), and isoprenylboronic acid (83.4 g, INTERMEDIATE 3). 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).

Workup

  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

Sources & evidence

ORD record
ord-d9d045efc71246a7886de28a8eee081e
Source dataset
uspto-grants-2013_05
Patent number
US08445480B2

Reaction notes

Loading…