Reacción #1876813

Ecuación de reacción

Compound ( c )

2-bromo-5-ethoxybenzotrifluoride

butyllithium hexane

hydrochloric acid

Triisopropyl borate

→

Compound ( d )

Rendimiento 89.1%

4-ethoxy-2-trifluoromethylphenylboric Acid

Rendimiento 89.1%

Disolventes

tetrahydrofuran

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas then slowly added dropwise at −78° C.
2. 2
   workup.STIRRINGthe mixture was stirred at the same temperature for 1 hour
3. 3
   TemperaturaThe temperature was increased to room temperature
4. 4
   Temperaturacooling temperature
5. 5
   Extracciónthe aqueous layer was extracted three times with ether
6. 6
   Lavadowashed with water
7. 7
   Secadodried over anhydrous magnesium sulfate
8. 8
   workup.DISTILLATIONThe solvent was distilled off under reduced pressure

Procedimiento

Compound (c) (10.0 g) dissolved in tetrahydrofuran (THF) (40 mL) was cooled to −78° C., a 1.6 M butyllithium/hexane solution (30 mL) was slowly added dropwise and the mixture was stirred at the same temperature for 2 hours. Triisopropyl borate (14.0 g) dissolved in THF (20 mL) was then slowly added dropwise at −78° C., and the mixture was stirred at the same temperature for 1 hour. The temperature was increased to room temperature and the final solution was stirred. After adding 3 M hydrochloric acid (200 mL) dropwise at ice-cooling temperature, the aqueous layer was extracted three times with ether. The organic layers were combined, washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 8.28 g of Compound (d).

Fuente