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

HRID 130409

Reaction equation

HRID 130409 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:18](I)[CH3:19]>CC(=O)CC>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:18][CH3:19])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 243644-Bromo-2-nitrophenol

Product 1

HCID 222831884-Bromo-1-ethoxy-2-nitrobenzene

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

4-Bromo-2-nitrophenol (5.0 g, 23 mmol) and potassium carbonate (9.52 g, 69 mmol) were suspended in 2-butanone (100 ml). Ethyl iodide (2.2 ml, 28 mmol) was added dropwise at room temperature and stirred for 30 minutes. The suspension was heated at reflux for 18 hours, cooled and filtered, and the residue washed with acetone. The filtrate was concentrated in vacuo to a crude solid that was used without further purification (D14). 1H-NMR (CDCl3) δ 7.42 (1H, d, J 2.5 Hz), 7.60 (1H, dd, J 9.0, 2.5 Hz), 6.96 (1H, d, J 9.0 Hz), 4.17 (2H, q, J 7.0 Hz), 1.47 (3H, t, J 7.0 Hz).

Workup

  1. temperatureThe suspension was heated
  2. temperatureat reflux for 18 hours
  3. temperaturecooled
  4. filtrationfiltered
  5. washthe residue washed with acetone
  6. concentrationThe filtrate was concentrated in vacuo to a crude solid that
  7. customwas used without further purification (D14)

Sources & evidence

ORD record
ord-fb9bc193cfa74a289e987198dbf5bdf9
Source dataset
uspto-grants-2008_06
Patent number
US07381728B2

Linked notes

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