Water → 2-Bromophenetole

HRID 1978732Notes

Reaction equation

HRID 1978732 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].O>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH2:16][CH3:17]

Participants

6

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 72442-BromophenolHCID 11430Potassium Carbonate

Product 1

HCID 685002-Bromophenetole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In DMF (120 ml) was dissolved 2-bromophenol (12 g). To the mixture was added potassium carbonate (12.5 g) and then was added iodoethane (6.7 ml), and the mixture was stirred at room temperature for 1 hour. The reaction mixture was added to water, and the mixture was extracted with ethyl acetate, washed with saturated brine and dried with magnesium sulfate. Under reduced pressure, the solvent was evaporated, and the residue was purified with silica gel column chromatography (hexane/ethyl acetate=12/1) to give 1-bromo-2-ethoxybenzene (12.2 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washwashed with saturated brine
  3. dry with materialdried with magnesium sulfate
  4. customUnder reduced pressure, the solvent was evaporated
  5. customthe residue was purified with silica gel column chromatography (hexane/ethyl acetate=12/1)

Sources & evidence

ORD record
ord-dcb5a628307e4f4baae551758a10c2c7
Source dataset
uspto-grants-2001_05
Patent number
US06235771B1

Reaction notes

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