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

HRID 1051856Notes

Reaction equation

HRID 1051856 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[OH:9].C(=O)([O-])[O-].[K+].[K+].I[CH2:17][CH3:18]>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[O:9][CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 27246002-Bromo-5-fluorophenol

Product 1

HCID 447549131-Bromo-2-ethoxy-4-fluorobenzeneYield 88.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 2-bromo-5-fluorophenol (5.0 g) in DMF (30 mL) was added potassium carbonate (10.8 g) and iodoethane (6.12 g). The mixture was stirred at room temperature for 16 h. The solvent was removed in vacuum. Water was added and the mixture was extracted with a mixture of ethyl acetate and hexane (3:1). The organic phase was washed with saturated sodium chloride solution, dried (sodium sulfate) and the solvent was removed in vacuum, to give 5.06 g of the title compound as a crude product, that was used for the next step without purification.

Workup

  1. customThe solvent was removed in vacuum
  2. additionWater was added
  3. extractionthe mixture was extracted with a mixture of ethyl acetate and hexane (3:1)
  4. washThe organic phase was washed with saturated sodium chloride solution
  5. dry with materialdried (sodium sulfate)
  6. customthe solvent was removed in vacuum

Sources & evidence

ORD record
ord-52d2959ced074be2b997d619aecfa5b9
Source dataset
uspto-grants-2016_07
Patent number
US09388177B2

Reaction notes

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