Potassium Carbonate → 2-((5-Fluoropyridin-3-yl)oxy)acetonitrile

HRID 56271Notes

Reaction equation

HRID 56271 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[N:6][CH:7]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:16][C:17]#[N:18]>CC#N>[F:1][C:2]1[CH:3]=[C:4]([O:8][CH2:16][C:17]#[N:18])[CH:5]=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 27629063-Fluoro-5-hydroxypyridine

Product 1

HCID 900242292-((5-Fluoropyridin-3-yl)oxy)acetonitrileYield 43%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of 5-fluoropyridin-3-ol (0.95 g, 8.40 mmol) and K2CO3 (1.16 g, 8.40 mmol) in CH3CN (6 mL) was added dropwise 2-bromoacetonitrile (1.01 g, 8.42 mmol) at rt and upon the end of addition the mixture was stirred at rt for 40 h. The mixture was filtered and the filtrate was concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=3:1) to give the title compound as a yellow solid (0.55 g, 43%).

Workup

  1. additionupon the end of addition the mixture
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=3:1)

Sources & evidence

ORD record
ord-de5aa9ef052047068fb0dd937cf32f93
Source dataset
uspto-grants-2016_09
Patent number
US09434695B2

Reaction notes

Loading…