Methyl iodide → Methyl 3-cyano-4-methoxybenzoate

HRID 1776353Notes

Reaction equation

HRID 1776353 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[OH:13])[C:6]([O:8][CH3:9])=[O:7])#[N:2].CI.[C:16]([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[O:13][CH3:16])[C:6]([O:8][CH3:9])=[O:7])#[N:2]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 11769089Methyl 3-cyano-4-hydroxybenzoate

Product 1

HCID 2801011Methyl 3-cyano-4-methoxybenzoateYield 52%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of methyl 3-cyano-4-hydroxybenzoate (2.0 g, 11.20 mmol) in DMF (20 mL) were added CH3I (2.40 g, 16.01 mmol) and K2CO3 (2.30 g, 16.01 mmol) at 0° c. under a N2 atmosphere. The reaction mixture was stirred at 80° C. for 2 h. After completion of starting material (monitored by TLC), reaction mixture was diluted with water and extracted with EtOAc (2×100 mL). The combined organic layers were washed with water (2×50 mL), brine and dried over anhydrous Na2SO4. After filtration and evaporation in vacuo, the crude material was purified by silica gel column chromatography to afford methyl 3-cyano-4-methoxybenzoate (1.1 g, 52%), as a pale yellow solid.

Workup

  1. customAfter completion of starting material (monitored by TLC), reaction mixture
  2. extractionextracted with EtOAc (2×100 mL)
  3. washThe combined organic layers were washed with water (2×50 mL), brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationAfter filtration and evaporation in vacuo
  6. customthe crude material was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-2ca7be4e954d4030acc0fc464776177a
Source dataset
uspto-grants-2016_02
Patent number
US09265767B2

Reaction notes

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