Iodoethane → 2-Bromophenetole

HRID 1289177Notes

Reaction equation

HRID 1289177 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].C([O-])([O-])=O.[K+].[K+].I[CH2:16][CH3:17]>CC(C)=O>[CH2:16]([O:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[Br:1])[CH3:17]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 72442-BromophenolHCID 11430Potassium Carbonate

Product 1

HCID 685002-BromophenetoleYield 88%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 2-bromophenol (1.3 ml, 0.012 mol) in 50 ml acetone was added K2CO3 (4.1 g, 0.03 mol) and iodoethane (1.0 ml, 0.013 mol). The reaction mixture was heated to reflux for 8 h, cooled to ambient temperature and filtered. The solvent was removed under reduced pressure and the residue was taken up in EtOAc. The organic phase was washed with 1N NaOH×2, water and brine. Drying over Na2SO4 afforded 2.1 g (88%) of 2-ethoxybromobenzene.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 8 h
  3. filtrationfiltered
  4. customThe solvent was removed under reduced pressure
  5. washThe organic phase was washed with 1N NaOH×2, water and brine
  6. dry with materialDrying over Na2SO4

Sources & evidence

ORD record
ord-21cd3c982ab14d909395378bf818c1a2
Source dataset
uspto-grants-1998_05
Patent number
US05747540

Reaction notes

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