Iodoethane → 4-Bromo-1-ethoxy-2-ethylbenzene

HRID 858775Notes

Reaction equation

HRID 858775 reaction equation
C(=O)([O-])[O-].[K+].[K+].I[CH2:8][CH3:9].[Br:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[C:13]([CH2:18][CH3:19])[CH:12]=1>CN(C=O)C>[Br:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:8][CH3:9])=[C:13]([CH2:18][CH3:19])[CH:12]=1

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 878774-Bromo-2-ethylphenol

Product 1

HCID 187120224-Bromo-1-ethoxy-2-ethylbenzeneYield 72%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (3.3 g, 23.6 mmol) followed by iodoethane (0.63 mL, 7.9 mmol) were added to a solution of 4-bromo-2-ethyl-phenol (1.6 g, 7.9 mmol) in DMF (10 mL). The mixture was stirred for 20 hours and then partitioned between 1N HCl and EtOAc. The organic layers were washed with saturated NaHCO3, brine, dried over Na2SO4 and concentrated. The crude yellow oil was purified by flash column chromatography (hexanes) to give the desired product (1.3 g, 72%).

Workup

  1. custompartitioned between 1N HCl and EtOAc
  2. washThe organic layers were washed with saturated NaHCO3, brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe crude yellow oil was purified by flash column chromatography (hexanes)

Sources & evidence

ORD record
ord-806423eaa7ba40b0901a32fd35f32607
Source dataset
uspto-grants-2006_12
Patent number
US07148226B2

Reaction notes

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