Dimethylformamide → 3-Phenoxy-5-(trifluoromethyl)picolinonitrile

HRID 1809597Notes

Reaction equation

HRID 1809597 reaction equation
Cl[C:2]1[C:3]([C:12]#[N:13])=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.O.O.O.[O-:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[Na+].CN(C=O)C>CCOCC>[O:17]([C:2]1[C:3]([C:12]#[N:13])=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 14733743-Chloro-5-(trifluoromethyl)pyridine-2-carbonitrileHCID 23681143Sodium Phenoxide Trihydrate

Product 1

HCID 674852863-Phenoxy-5-(trifluoromethyl)picolinonitrileYield 67.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
80 °C

Procedure

3-Chloro-5-(trifluoromethyl)picolinonitrile (0.220 g, 1.07 mmol) was combined with sodium phenoxide trihydrate (0.272 g, 1.60 mmol) and DMF (5 mL). The resulting mixture was heated to 80° C. and agitated for one hour. The mixture was then cooled, diluted with ether and washed with 1M NaOH, water (3×), brine, dried and evaporated to give crude 3-phenoxy-5-(trifluoromethyl)picolinonitrile (0.190 g, 67.5% yield) as red oil.

Workup

  1. temperatureThe mixture was then cooled
  2. washwashed with 1M NaOH, water (3×), brine
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-cf45a6206dbd441bbbec73d4dd1a5671
Source dataset
uspto-grants-2013_01
Patent number
US08362037B2

Reaction notes

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