Reaction #710498

Reaction equation

2-chloro-6-(trifluoromethyl)nicotinic acid

BH3-THF

→

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

Solvents

NaHCO3

THF

Conditions

Workup

1. 1
   ConcentrationAfter 16 h the reaction mixture was concentrated under reduced pressure
2. 2
   Otherto remove THF
3. 3
   OtherThe resulting reaction mixture
4. 4
   Extractionextracted with ethyl acetate (2×500 mL)
5. 5
   WashThe combined organic layers were washed with water (500 mL), brine (500 mL)
6. 6
   Dryingdried over anhydrous sodium sulfate
7. 7
   Otherthe solvent was removed under reduced pressure

Procedure

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%).

Source