N-methyl-2-pyrrolidone → 2-Fluoro-5-methoxybenzonitrile

HRID 844008

Reaction equation

HRID 844008 reaction equation
Cl[C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[F:10].[C:11]([Cu])#[N:12].CN1CCCC1=O>C(Cl)Cl>[F:10][C:3]1[CH:4]=[CH:5][C:6]([O:8][CH3:9])=[CH:7][C:2]=1[C:11]#[N:12]

Participants

5

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 27735853-Chloro-4-fluoroanisoleHCID 178418546HCID 178418546, compound2×

Product 1

HCID 27745462-Fluoro-5-methoxybenzonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-Chloro-1-fluoro-4-methoxy-benzene (10.4 grams, 65.0 mmole), CuCN (6.4 grams, 71.0 mmole) and N-methylpyrrolidinone (100 ml) was refluxed for 18 hours. An additional 2.3 g CuCN was added, and the mixture was refluxed for 40 hours. The mixture was poured into 300 ml ice water and stirred for 10 minutes. This was poured into 100 ml methylene chloride and the layers were separated. The mixture was washed with water, dried over MgSO4, filtered, and concentrated to a solid (2.8 g). MW 137.12; MS (m/e) 137(M+).

Workup

  1. temperaturethe mixture was refluxed for 40 hours
  2. customthe layers were separated
  3. washThe mixture was washed with water
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to a solid (2.8 g)

Sources & evidence

ORD record
ord-3975cb63a80e47fcaea38a24e043d76d
Source dataset
uspto-grants-2002_04
Patent number
US06380218B1

Linked notes

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