Methyl iodide → 1-(3-Bromo-5-chloro-4-fluoro-2-methoxyphenyl)ethanone

HRID 2274115Notes

Reaction equation

HRID 2274115 reaction equation
[Br:1][C:2]1[C:3]([OH:13])=[C:4]([C:10](=[O:12])[CH3:11])[CH:5]=[C:6]([Cl:9])[C:7]=1[F:8].[C:14](=O)([O-])[O-].[K+].[K+].CI>CN(C)C=O>[Br:1][C:2]1[C:3]([O:13][CH3:14])=[C:4]([C:10](=[O:12])[CH3:11])[CH:5]=[C:6]([Cl:9])[C:7]=1[F:8]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 866668921-(3-Bromo-5-chloro-4-fluoro-2-hydroxyphenyl)ethanone

Product 1

HCID 866669121-(3-Bromo-5-chloro-4-fluoro-2-methoxyphenyl)ethanoneYield 39%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 1-(3-bromo-5-chloro-4-fluoro-2-hydroxyphenyl)ethanone (5.3 g, 20 mmol), potassium carbonate (7.2 g, 52 mmol) and methyl iodide (2.7 mL, 44 mmol) in N,N-dimethylformamide (20 mL) was heated at 60° C. for 1 hour. The mixture was filtered and washed with ethyl acetate. The filtrate was diluted with water and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, and evaporated to dryness. The residue was purified on silica gel, eluting with 0 to 20% ethyl acetate in hexane, to yield the desired product (39% yield). LCMS calculated for C9H8BrClFO2 (M+H)+: m/z=280.9, 282.9. found: 280.8, 282.8.

Workup

  1. filtrationThe mixture was filtered
  2. washwashed with ethyl acetate
  3. additionThe filtrate was diluted with water
  4. extractionextracted with ethyl acetate
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over sodium sulfate
  7. customevaporated to dryness
  8. customThe residue was purified on silica gel
  9. washeluting with 0 to 20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-d3767ad2229a4eeb9428ca1e18daf6de
Source dataset
uspto-grants-2015_09
Patent number
US09126948B2

Reaction notes

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