Methyl iodide → HCID 86666944, compound

HRID 1499886Notes

Reaction equation

HRID 1499886 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)C=O.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 N,N-dimethylformamide (40 mL)was treated with methyl iodide (6.4 mL, 100 mmol) and stirred at 60° C. for 1 h. The reaction mixture was diluted with water and extracted with ethyl acetate (2×). 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 ethyl acetate in hexanes (5%-30%) to give the desired product (14 g, 84%) as an orange solid. 1H NMR (300 MHz, CDCl3) δ 7.69 (s, 1H), 3.79 (s, 3H), 2.60 (s, 3H). LCMS for C9H8Cl2IO2 (M+H)+: m/z=344.9, 346.9; Found: 344.8, 346.9.

Workup

  1. extractionextracted with ethyl acetate (2×)
  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-ae97c5d7d19147ccb798da4aef3c9530
Source dataset
uspto-grants-2015_12
Patent number
US09199982B2

Reaction notes

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