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

HRID 510917Notes

Reaction equation

HRID 510917 reaction equation
[Br:1][C:2]1[C:3]([OH:12])=[C:4]([C:9](=[O:11])[CH3:10])[CH:5]=[C:6]([Cl:8])[CH:7]=1.[C:13](=O)([O-])[O-].[K+].[K+].CI>CN(C)C=O.O>[Br:1][C:2]1[C:3]([O:12][CH3:13])=[C:4]([C:9](=[O:11])[CH3:10])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 27355463'-Bromo-5'-chloro-2'-hydroxyacetophenone

Product 1

HCID 162280241-(3-Bromo-5-chloro-2-methoxyphenyl)ethanoneYield 96.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 1-(3-bromo-5-chloro-2-hydroxyphenyl)ethanone (5.0 g, 20 mmol) in N,N-dimethylformamide (40 mL) was treated with potassium carbonate (5.5 g, 40 mmol) followed by methyl iodide (1.9 mL, 30 mmol) and heated at 60° C. overnight. The reaction mixture was diluted with water (300 mL) and extracted with ethyl acetate (2×150 mL). The organic layers were washed with water (3×100 mL) and brine, dried with sodium sulfate, filtered, and concentrated to give the crude product. Purification by flash column chromatography using ethyl acetate in hexanes (0%-5%-25%) gave the desired product (5.1 g, 96%). LCMS for C9H9BrClO2 (M+H)+: m/z=262.9, 264.9. Found: 262.9, 264.9.

Workup

  1. extractionextracted with ethyl acetate (2×150 mL)
  2. washThe organic layers were washed with water (3×100 mL) and brine
  3. dry with materialdried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give the crude product
  7. customPurification by flash column chromatography

Sources & evidence

ORD record
ord-b51287cd9d5042dd8c9a0b51afc8d760
Source dataset
uspto-grants-2015_08
Patent number
US09096600B2

Reaction notes

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