Methyl iodide → 5-Bromo-2-methoxybenzonitrile

HRID 2173235Notes

Reaction equation

HRID 2173235 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:10])=[C:6]([CH:9]=1)[C:7]#[N:8].CI.[C:13]([O-])([O-])=O.[K+].[K+]>CC#N>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH3:13])=[C:6]([CH:9]=1)[C:7]#[N:8]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 27570145-Bromo-2-hydroxybenzonitrile

Product 1

HCID 44185605-Bromo-2-methoxybenzonitrile

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 5-bromo-2-hydroxybenzonitrile (1 g, 5 mmol), MeI (0.85 g, 6 mmol) and K2CO3 (2 g, 15 mmol) in 25 mL of dry CH3CN were heated to refluxed over night. The solvent was evaporated off and the residue was added water. Extracted the mixture with DCM and the organic layer was washed with saturated chloride, dried over Na2SO4. The residue was purified with fast column chromatograph to afford compound 5-bromo-2-methoxybenzonitrile.

Workup

  1. temperaturewere heated
  2. temperatureto refluxed over night
  3. customThe solvent was evaporated off
  4. additionthe residue was added water
  5. extractionExtracted the mixture with DCM
  6. washthe organic layer was washed with saturated chloride
  7. dry with materialdried over Na2SO4
  8. customThe residue was purified with fast column chromatograph

Sources & evidence

ORD record
ord-01c63ced46dd4886bcc4a656eddd955b
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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