Methyl iodide → 1-(5-Chloro-4-fluoro-3-iodo-2-methoxyphenyl)ethanone

HRID 1499685Notes

Reaction equation

HRID 1499685 reaction equation
[Cl:1][C:2]1[C:3]([F:13])=[C:4]([I:12])[C:5]([OH:11])=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1.CI.[C:16](=O)([O-])[O-].[K+].[K+]>CN(C)C=O.CCOCC>[Cl:1][C:2]1[C:3]([F:13])=[C:4]([I:12])[C:5]([O:11][CH3:16])=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 866668571-(5-Chloro-4-fluoro-2-hydroxy-3-iodophenyl)ethanone

Product 1

HCID 866668581-(5-Chloro-4-fluoro-3-iodo-2-methoxyphenyl)ethanoneYield 74.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

1-(5-Chloro-4-fluoro-2-hydroxy-3-iodophenyl)ethanone (13 g, 41 mmol) was dissolved in N,N-dimethylformamide (41.3 mL). Methyl iodide (3.9 mL, 62 mmol) was added followed by potassium carbonate (11 g, 83 mmol). The reaction was heated at 60° C. for 1 hour. The mixture was cooled to room temperature, diluted with ether. The organic layers were separated and combined, washed with water, dried over MgSO4, concentrated and purified on silica gel (eluting with 0 to 10% EtOAc in hexanes) to give the desired product (10 g, 70%). LCMS calculated for C9H8ClFIO2 (M+H)+: m/z=328.9; Found: 328.9.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customThe organic layers were separated
  3. washwashed with water
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. custompurified on silica gel (eluting with 0 to 10% EtOAc in hexanes)

Sources & evidence

ORD record
ord-c27bd1c44c4b44c58c937a37a7ae7387
Source dataset
uspto-grants-2015_12
Patent number
US09199982B2

Reaction notes

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