Reaction #1596953

Reaction equation

bromodibenzofuran

Compound 16-1

bromodibenzofuran

pyrazole

salicylaldoxime

cesium carbonate

→

Compound 17-1

Yield 78.0%

Pyrazolyldibenzofuran

Yield 78.0%

Solvents

DMF

Conditions

Workup

1. 1
   Otheris reacted
2. 2
   Temperatureunder reflux
3. 3
   Temperaturewith heating for 6 hours
4. 4
   workup.DISTILLATIONDMF is distilled off from the resulting mixture
5. 5
   Temperatureby heating under reduced pressure
6. 6
   workup.ADDITIONEthyl acetate is added to the residue
7. 7
   Filtrationthe mixture is filtered with Celite
8. 8
   workup.ADDITIONa 1M sodium hydroxide aqueous solution is added to the obtained liquid
9. 9
   ExtractionOrganic layers extracted from the obtained mixture with ethyl acetate
10. 10
    Dryingare dried with sodium sulfate
11. 11
    ConcentrationThe organic layers are concentrated

Procedure

Under nitrogen current, a mixture containing 12.35 g (50 mmol) of bromodibenzofuran (Compound 16-1), 5.11 g (75 mmol) of pyrazole, 358 mg (2.5 mmol) of cuprous oxide (I), 1.37 g (10 mmol) of salicylaldoxime, 32.6 g (100 mmol) of cesium carbonate, and 100 ml of DMF is reacted under reflux with heating for 6 hours. DMF is distilled off from the resulting mixture by heating under reduced pressure. Ethyl acetate is added to the residue and the mixture is filtered with Celite, and a 1M sodium hydroxide aqueous solution is added to the obtained liquid. Organic layers extracted from the obtained mixture with ethyl acetate are dried with sodium sulfate. The organic layers are concentrated and refined by silica gel column chromatography to obtain 9.12 g (39 mmol) of Compound 17-1.

Source