Methyl iodide → HCID 86666944, compound

HRID 511023Notes

Reaction equation

HRID 511023 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([C:9](=[O:11])[CH3:10])=[C:4]([OH:12])[C:3]=1[I:13].[C:14](=O)([O-])[O-].[K+].[K+].CI>CN(C=O)C.O>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([C:9](=[O:11])[CH3:10])=[C:4]([O:12][CH3:14])[C:3]=1[I:13]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 86666943HCID 86666943, compound

Product 1

HCID 86666944HCID 86666944, compoundYield 86.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 1-(4,5-dichloro-2-hydroxy-3-iodophenyl)ethanone (16 g, 47 mmol) and potassium carbonate (17 g, 120 mmol) in DMF (40 mL) was treated with methyl iodide (6.4 mL, 100 mmol) and stirred at 60° C. for 1 hour. The reaction mixture was diluted with water and extracted with EtOAc (twice). The combined organic layers were dried with magnesium sulfate, filtered, and concentrated to give a crude solid. The crude material was purified by flash column chromatography using EtOAc in hexanes (5%-30%) to give the desired product (14 g, 84%) as an orange solid. LCMS for C9H8Cl2IO2 (M+H)+: m/z=344.9, 346.9. Found: 344.8, 346.9.

Workup

  1. extractionextracted with EtOAc (twice)
  2. dry with materialThe combined organic layers were dried with magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give a crude solid
  6. customThe crude material was purified by flash column chromatography

Sources & evidence

ORD record
ord-9d7f8233f46b4916a7eba47ebe5a4d66
Source dataset
uspto-grants-2015_08
Patent number
US09096600B2

Reaction notes

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