Isopropyl iodide → 1,2-Difluoro-4-isopropoxybenzene

HRID 1728016Notes

Reaction equation

HRID 1728016 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[CH:17]([CH3:19])[CH3:18]>CC(C)=O>[F:8][C:7]1[CH:6]=[CH:5][C:4]([O:9][CH:17]([CH3:19])[CH3:18])=[CH:3][C:2]=1[F:1]

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 759273,4-Difluorophenol

Product 1

HCID 27741951,2-Difluoro-4-isopropoxybenzeneYield 92.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 3,4-difluoro-phenol (5 g, 38.4 mmol) in acetone (50 mL) was added potassium carbonate (54 g, 38.4 mmol) and 2-iodo-propane. The reaction mixture was heated at refluxing for 24 h. The crude was cooled down and filtered through a short pad of celite. The filtrate was concentrated and the residue was purified by chromatography (EtOAc:Hexanes=1:9) to give 1,2-difluoro-4-isopropoxy-benzene as colorless oil (Yield 6.12 g, 92.3%).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat refluxing for 24 h
  3. temperatureThe crude was cooled down
  4. filtrationfiltered through a short pad of celite
  5. concentrationThe filtrate was concentrated
  6. customthe residue was purified by chromatography (EtOAc:Hexanes=1:9)

Sources & evidence

ORD record
ord-9e8529ec4f894edb8625c10afd42eea9
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

Loading…