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

HRID 1387225Notes

Reaction equation

HRID 1387225 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-4fde6b7f1dde44a6b811bb60cbea9b08
Source dataset
uspto-grants-2001_07
Patent number
US06268310B1

Reaction notes

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