Réaction #2348101

Équation de réaction

hydrochloric acid

sec-BuLi

compound ( 22 )

3,4-difluoro-5-(4-pentylphenyl)toluene

DMF

→

2,3-difluoro-4-(4-pentylphenyl)-6-methylbenzaldehyde

Rendement 77.3%

Solvants

THF

THF

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONwas added
2. 2
   workup.ADDITIONwas added
3. 3
   workup.STIRRINGby stirring at −78° C. for 1 hour
4. 4
   workup.STIRRINGstirring over night
5. 5
   Extractionthe aqueous layer was extracted with toluene, which
6. 6
   workup.ADDITIONwas added to the organic layer
7. 7
   LavageThe organic layer was washed with saturated saline
8. 8
   Séchagedried over anhydrous magnesium sulfate
9. 9
   workup.DISTILLATIONThe solvent was distilled off

Mode opératoire

Under a nitrogen atmosphere, 8.93 g of the compound (22) having been dissolved in 66 mL of THF was cooled to −78° C., to which 39.0 mL of sec-BuLi (1 M/L) was added, followed by stirring at the same temperature for 2 hours. 3.56 g of DMF having been dissolved in 44 mL of THF was added thereto, followed by stirring at −78° C. for 1 hour, and after increasing the temperature to room temperature, stirring over night. 20 mL of 3N hydrochloric acid was added thereto, and the aqueous layer was extracted with toluene, which was added to the organic layer. The organic layer was washed with saturated saline and dried over anhydrous magnesium sulfate. The solvent was distilled off to obtain 7.61 g of 2,3-difluoro-4-(4-pentylphenyl)-6-methylbenzaldehyde (23).

Source