2-Chloro-6-fluorobenzonitrile → 2-Chloro-6-methoxybenzonitrile

HRID 1597174Notes

Reaction equation

HRID 1597174 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6](F)[C:3]=1[C:4]#[N:5].[CH3:11][O-:12].[Na+]>CO>[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([O:12][CH3:11])[C:3]=1[C:4]#[N:5]

Participants

4

Reactant 2

HCID 695872-Chloro-6-fluorobenzonitrileHCID 10942334Sodium Methoxide

Product 1

HCID 810552-Chloro-6-methoxybenzonitrileYield 98.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-Chloro-6-fluorobenzonitrile (Aldrich, 5.0 g, 32.1 mmol) was dissolved in MeOH (100 mL), NaOMe (7.4 mL of 25% wt. solution, 32.1 mmol) and refluxed 18 h. The mixture was concentrated poured into EtOAc/H2O and extracted with EtOAc to give the title compound (5.3 g, 59%).

Workup

  1. concentrationThe mixture was concentrated
  2. additionpoured into EtOAc/H2O
  3. extractionextracted with EtOAc

Sources & evidence

ORD record
ord-699121cca38b40abb0b9e82bd898b154
Source dataset
uspto-grants-2001_09
Patent number
US06294531B1

Reaction notes

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