Reacción #710498

Ecuación de reacción

2-chloro-6-(trifluoromethyl)nicotinic acid

BH3-THF

→

[2-chloro-6-(trifluoromethyl)pyridin-3-yl]methanol

Disolventes

NaHCO3

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   ConcentraciónAfter 16 h the reaction mixture was concentrated under reduced pressure
2. 2
   Otroto remove THF
3. 3
   OtroThe resulting reaction mixture
4. 4
   Extracciónextracted with ethyl acetate (2×500 mL)
5. 5
   LavadoThe combined organic layers were washed with water (500 mL), brine (500 mL)
6. 6
   Secadodried over anhydrous sodium sulfate
7. 7
   Otrothe solvent was removed under reduced pressure

Procedimiento

To a stirred solution of e 2-chloro-6-(trifluoromethyl)nicotinic acid (Int-15) (40 g, 1.0 eq.) in THF (400 mL) was added BH3-THF (266.6 mL, 1.5 eq) at room temperature. The progress of the reaction was monitored by TLC. After 16 h the reaction mixture was concentrated under reduced pressure to remove THF. The resulting reaction mixture was diluted with 10% NaHCO3 (500 mL) and extracted with ethyl acetate (2×500 mL). The combined organic layers were washed with water (500 mL), brine (500 mL), dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure to get crude [2-chloro-6-(trifluoromethyl)pyridin-3-yl]methanol (Int-16) as light yellow liquid, 32 g (85.5%).

Fuente