Reacción #2348101

Ecuación de reacción

hydrochloric acid

sec-BuLi

compound ( 22 )

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

DMF

→

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

Rendimiento 77.3%

Disolventes

THF

THF

Condiciones de reacción

Tratamiento posterior

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
   Extracciónthe aqueous layer was extracted with toluene, which
6. 6
   workup.ADDITIONwas added to the organic layer
7. 7
   LavadoThe organic layer was washed with saturated saline
8. 8
   Secadodried over anhydrous magnesium sulfate
9. 9
   workup.DISTILLATIONThe solvent was distilled off

Procedimiento

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).

Fuente