Methyl iodide → 4-Bromo-2-ethyl-1-methoxybenzene

HRID 858616Notes

Reaction equation

HRID 858616 reaction equation
[C:1](=[O:4])([O-])[O-].[K+].[K+].CI.[Br:9][C:10]1[CH:15]=[CH:14][C:13](O)=[C:12]([CH2:17][CH3:18])[CH:11]=1>CN(C=O)C>[Br:9][C:10]1[CH:15]=[CH:14][C:13]([O:4][CH3:1])=[C:12]([CH2:17][CH3:18])[CH:11]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 878774-Bromo-2-ethylphenol

Product 1

HCID 133016024-Bromo-2-ethyl-1-methoxybenzeneYield 68%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (3.9 g, 28.3 mmol) and methyl iodide (0.59 mL, 9.43 mmol) were added to a solution of 4-Bromo-2-ethyl-phenol (1.9 g, 9.43 mmol, from step 1 of Example A(22)) dissolved in DMF (10 mL). The mixture was stirred for 16 h under N2 and then partitioned between 1 N HCl and EtOAc. The organic layer was washed with saturated NaHCO3, brine, dried over Na2SO4 and concentrated to a yellow oil. The oil was purifed by silica gel chromatography to give the title compound as a clear oil (1.37 g, 68%).

Workup

  1. custompartitioned between 1 N HCl and EtOAc
  2. washThe organic layer was washed with saturated NaHCO3, brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated to a yellow oil

Sources & evidence

ORD record
ord-9d3e6d4046cf4d2da498da6a3b3b13f7
Source dataset
uspto-grants-2006_12
Patent number
US07148226B2

Reaction notes

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