Iodoethane → 4-Ethoxy-1,2-difluorobenzene

HRID 1728033Notes

Reaction equation

HRID 1728033 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[F:8].C(=O)([O-])[O-].[K+].[K+].I[CH2:17][CH3:18]>CN(C)C=O>[CH2:17]([O:9][C:4]1[CH:5]=[CH:6][C:7]([F:8])=[C:2]([F:1])[CH:3]=1)[CH3:18]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 759273,4-Difluorophenol

Product 1

HCID 27741874-Ethoxy-1,2-difluorobenzeneYield 90.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3,4-difluoro-phenol (10 g, 77 mmol) in N,N-dimethylformamide (50 mL) was added potassium carbonate (20 g, 145 mmol) and iodoethane (50 g, 320 mmol, Aldrich). The reaction mixture was heated at refluxing for 48 h. The crude was cooled to room temperature and filtered through a short pad of celite. The filtrate was concentrated and the residue was purified by chromatography (EtOAc:Hexanes=1:8) to give 4-ethoxy-1,2-difluoro-benzene as colorless oil (Yield 11 g, 90%).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat refluxing for 48 h
  3. filtrationfiltered through a short pad of celite
  4. concentrationThe filtrate was concentrated
  5. customthe residue was purified by chromatography (EtOAc:Hexanes=1:8)

Sources & evidence

ORD record
ord-134bd00a266d40939258940d354f2435
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

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