Reacción #43678

Ecuación de reacción

ammonium chloride

3-bromofluorobenzene

diisopropylamine

n-butyllithium

tetrahydrofuran

→

title compound

2-Bromo-6-fluorobenzaldehyde

Disolventes

water

N,N-dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGthe mixture was stirred at the same temperature for 1 hour
2. 2
   workup.STIRRINGthe mixture was stirred at the same temperature for 10 minutes
3. 3
   workup.STIRRINGthe mixture was stirred under ice-
4. 4
   Temperaturacooling for 5 minutes
5. 5
   Extracciónthe mixture was extracted with diethyl ether
6. 6
   LavadoThe extract washed with water and brine
7. 7
   Secadodried over anhydrous magnesium sulfate
8. 8
   Otrothe solvent was removed under reduced pressure

Procedimiento

To a solution of diisopropylamine (2.65 mL) in tetrahydrofuran (30 mL) was added n-butyllithium (2.44 mol/L n-hexane solution, 7.03 mL) at −78° C. under an argon atmosphere, and the mixture was stirred at the same temperature for 5 minutes. To the reaction mixture was added 3-bromofluorobenzene (3 g), and the mixture was stirred at the same temperature for 1 hour. To the reaction mixture was added N,N-dimethylformamide (1.45 mL), and the mixture was stirred at the same temperature for 10 minutes, then a saturated ammonium chloride aqueous solution was added to the reaction mixture, and the mixture was stirred under ice-cooling for 5 minutes. The mixture was poured into water, and the mixture was extracted with diethyl ether. The extract washed with water and brine and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to give the title compound (3.43 g).

Fuente