Borane;tetrahydrofuran → [2-Chloro-6-(trifluoromethyl)pyridin-3-yl]methanol

HRID 623316Notes

Reaction equation

HRID 623316 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].B.C1COCC1>C1COCC1.C([O-])(O)=O.[Na+]>[Cl:1][C:2]1[C:3]([CH2:4][OH:5])=[CH:7][CH:8]=[C:9]([C:11]([F:12])([F:13])[F:14])[N:10]=1

Participants

5

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 27782102-Chloro-6-(trifluoromethyl)nicotinic acid

Product 1

HCID 53256696[2-Chloro-6-(trifluoromethyl)pyridin-3-yl]methanol

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

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%).

Workup

  1. concentrationAfter 16 h the reaction mixture was concentrated under reduced pressure
  2. customto remove THF
  3. customThe resulting reaction mixture
  4. extractionextracted with ethyl acetate (2×500 mL)
  5. washThe combined organic layers were washed with water (500 mL), brine (500 mL)
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-d11eef648f3645f785f27b249355fa45
Source dataset
uspto-grants-2016_04
Patent number
US09301526B2

Reaction notes

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