Methyl iodide → HCID 86677830, compound

HRID 1499909Notes

Reaction equation

HRID 1499909 reaction equation
[C:1]([C:4]1[CH:11]=[C:10]([CH3:12])[C:7]([C:8]#[N:9])=[C:6]([I:13])[C:5]=1[OH:14])(=[O:3])[CH3:2].[C:15](=O)([O-])[O-].[K+].[K+].CI>CN(C)C=O.C(OCC)(=O)C>[C:1]([C:4]1[CH:11]=[C:10]([CH3:12])[C:7]([C:8]#[N:9])=[C:6]([I:13])[C:5]=1[O:14][CH3:15])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 86677824HCID 86677824, compound

Product 1

HCID 86677830HCID 86677830, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

The 4-acetyl-3-hydroxy-2-iodo-6-methylbenzonitrile (5.0 g, 17 mmol) was dissolved in N,N-dimethylformamide (50 mL) and the potassium carbonate (4.6 g, 33 mmol) and methyl iodide (2.1 mL, 33 mmol) were added. The reaction was heated to 60° C. and monitored by LC/MS. After heating for 2 hrs the reaction was complete. This was allowed to cool, diluted with ethyl acetate (300 mL) and filtered to remove the remaining solids. The organic layer was washed with water (3×), brine, dried over magnesium sulfate and concentrated to give the crude product as a dark solid. The product was purified by FCC on silica gel eluting hexane:ethyl acetate gradient to give 4-acetyl-3-methoxy-2-iodo-6-methylbenzonitrile as a pale yellow crystalline solid (5.0 g, 96%). LCMS calculated for C11H11INO2 (M+H)+: m/z=315.9; found: 316.0.

Workup

  1. temperatureAfter heating for 2 hrs the reaction
  2. temperatureto cool
  3. filtrationfiltered
  4. customto remove the remaining solids
  5. washThe organic layer was washed with water (3×), brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated
  8. customto give the crude product as a dark solid
  9. customThe product was purified by FCC on silica gel
  10. washeluting hexane

Sources & evidence

ORD record
ord-47f99918dc64418dad1f4bff70dcc000
Source dataset
uspto-grants-2015_12
Patent number
US09199982B2

Reaction notes

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