Methyl iodide → 3-Chloro-4-methoxybenzonitrile

HRID 1722004Notes

Reaction equation

HRID 1722004 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[C:5]#[N:6].[H-].[Na+].[CH3:13]I>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:13])[C:5]#[N:6]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 2735739Benzonitrile, 3-chloro-4-hydroxy-

Product 1

HCID 43231053-Chloro-4-methoxybenzonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
70 °C

Procedure

Under N2, a solution of 3-chloro-4-hydroxybenzonitrile (15.4 g, 0.1 mole) in dry DMF (75 ml) was added rapidly dropwise to a stirred suspension of sodium hydride (4.0 g, 0.1 mole, 60% oil dispersion) in dry DMF (25 ml). After heating at 70° C. for 2 hours, the mixture was cooled to 20° C. and a solution of methyliodide (30 ml) in dry DMF (50 ml) was added dropwise. Following an 18 hour period at room temperature, the precipitate of sodium iodide was removed by filtration and the solvent was stripped from the filtrate under reduced pressure. The crystalline residue was slurried in water and the product was collected to yield 16.8 g (quant.) of 26, m.p. 105°-108° C. A sample recrystallized from IPA-H2O melted at 107°-109° C.

Workup

  1. temperaturethe mixture was cooled to 20° C.
  2. customthe precipitate of sodium iodide was removed by filtration
  3. customthe product was collected

Sources & evidence

ORD record
ord-2ca80727694d46209dfa5cb8e5552917
Source dataset
uspto-grants-1989_08
Patent number
US04853383

Reaction notes

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