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

HRID 510943Notes

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=O)C.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

Conditions

Temperature: 60 °C

Procedure

1-(5-Chloro-4-fluoro-2-hydroxy-3-iodophenyl)ethanone (13 g, 41 mmol) was dissolved in DMF (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, washed with water, dried over MgSO4, concentrated. The residue was 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

temperatureThe mixture was cooled to room temperature
washwashed with water
dry with materialdried over MgSO4
concentrationconcentrated
customThe residue was purified on silica gel (eluting with 0 to 10% EtOAc in hexanes)

Sources & evidence

ORD record: ord-15c7d67cdaf84cf3ae8ad47e9b46fe07
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096600B2

Reaction notes

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