Water → 1,2-Dibromo-5-ethoxy-3-fluoro-4-methoxybenzene

HRID 1295943Notes

Reaction equation

HRID 1295943 reaction equation
[Br:1][C:2]1[C:3]([F:13])=[C:4]([OH:12])[C:5]([O:9][CH2:10][CH3:11])=[CH:6][C:7]=1[Br:8].CI.[C:16](=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[Br:8][C:7]1[CH:6]=[C:5]([O:9][CH2:10][CH3:11])[C:4]([O:12][CH3:16])=[C:3]([F:13])[C:2]=1[Br:1]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 229297133,4-Dibromo-6-ethoxy-2-fluorophenol

Product 1

HCID 229297021,2-Dibromo-5-ethoxy-3-fluoro-4-methoxybenzeneYield 46.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

After dissolving 3,4-dibromo-6-ethoxy-2-fluorophenol (3.8 g, 12 mmol) in dimethylformamide (30 ml), methyl iodide (1.5 ml, 24 mmol) and potassium carbonate (3.3 g, 24 mmol) were added and the mixture was stirred at room temperature for 18 hours. Water (80 ml) was added, extraction was performed with diethyl ether (60 ml×2), and then after washing the combined organic layers with brine (80 ml) and drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate) to yield the title compound (1.83 g, 46.7%).

Workup

  1. additionwere added
  2. extractionextraction
  3. washafter washing the combined organic layers with brine (80 ml)
  4. dry with materialdrying over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate)

Sources & evidence

ORD record
ord-e57dee425b8b4b5ca6cb81a8f5234db9
Source dataset
uspto-grants-2007_07
Patent number
US07244730B2

Reaction notes

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