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

HRID 1453229Notes

Reaction equation

HRID 1453229 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%). 1H NMR (400 MHz, CDCl3): δ 1.18 (t, J=7.3 Hz, 3H), 1.41 (t, J=7.1 Hz, 3H), 2.60 (q, J=7.6 Hz, 2H), 3.99 (q, J=7.1 Hz, 2H), 6.68 (d, J=8.1 Hz, 1H), 7.24 (m, 2H).

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-e5fdd7490118496cb9c2d6abc915c05f
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Reaction notes

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