Water → 2-Phenyl-4-(2,6-difluorophenyl)oxazole

HRID 1871892Notes

Reaction equation

HRID 1871892 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]([F:12])[C:3]=1[C:4](=O)[CH2:5]Br.[C:13]([NH2:21])(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.O>CC1C=CC=CC=1C>[C:14]1([C:13]2[O:20][CH:5]=[C:4]([C:3]3[C:2]([F:1])=[CH:11][CH:10]=[CH:9][C:8]=3[F:12])[N:21]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 962WaterHCID 2331BenzamideHCID 27782632,6-Difluorophenacyl bromide

Product 1

HCID 217155952-Phenyl-4-(2,6-difluorophenyl)oxazoleYield 121.8%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

5.7 g 2,6-difluorophenacyl bromide and 3.63 g benzamide were suspended in 20 ml o-xylene, and the suspension was subjected to reflux under heating for 1.5 hours. After completing the reaction, the suspension reacted was added with water, then extracted with ethyl acetate and further washed with saturated saline solution. The organic layer obtained was dried with anhydrous magnesium sulfate, and the solvent used was removed by distillation under reduced pressure. Out of 7.6 g residue obtained, 1.0 g thereof was purified by using silica gel column chromatography, affording the objective substance in an amount of 0.6 g.

Workup

  1. temperatureto reflux
  2. temperatureunder heating for 1.5 hours
  3. customthe reaction
  4. customthe suspension reacted
  5. extractionextracted with ethyl acetate
  6. washfurther washed with saturated saline solution
  7. customThe organic layer obtained
  8. dry with materialwas dried with anhydrous magnesium sulfate
  9. customthe solvent used was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-f0c6ddac7a794ded872e54d73be69c50
Source dataset
uspto-grants-2000_08
Patent number
US06107251

Reaction notes

Loading…