Potassium Iodide → 3,4-Difluoro-4'-(2-methoxyethoxy)biphenyl

HRID 747074Notes

Reaction equation

HRID 747074 reaction equation
[F:1][CH:2]1[C:7]([F:9])(O)[CH:6]=[CH:5][C:4]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:3]1.Br[CH2:17][CH2:18][O:19][CH3:20].[I-].[K+].C(=O)([O-])[O-:24].[K+].[K+]>CC(=O)CC>[F:1][C:2]1[CH:3]=[C:4]([C:10]2[CH:15]=[CH:14][C:13]([O:24][CH2:17][CH2:18][O:19][CH3:20])=[CH:12][CH:11]=2)[CH:5]=[CH:6][C:7]=1[F:9]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 809722-Bromoethyl methyl etherHCID 693013543,4-Difluoro-4-hydroxybiphenyl

Product 1

HCID 117371393,4-Difluoro-4'-(2-methoxyethoxy)biphenylYield 23.4%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 3,4-difluoro-1,1′-biphenyl-4-ol (0.50 g, 2.43×10−3 mol) of 1-bromo-2-methoxyethane (0.34 g, 2.43×10−3 mol), potassium iodide (0.04 g, 2.43×10−4 mol), potassium carbonate (1.34 g, 9.72×10−3 mol) and butanone (20 cm3) was then heated overnight under reflux. The mixture was filtered to remove inorganic material and the filtrate evaporated down under reduced pressure. The crude product was purified by column chromatography on silica gel using dichloromethane as the eluent and recrystallisation from hexane to give the pure (GC: 100%) desired product (0.15 g 23%).

Workup

  1. temperaturewas then heated overnight
  2. temperatureunder reflux
  3. filtrationThe mixture was filtered
  4. customto remove inorganic material
  5. customthe filtrate evaporated down under reduced pressure
  6. customThe crude product was purified by column chromatography on silica gel
  7. customas the eluent and recrystallisation from hexane

Sources & evidence

ORD record
ord-9d13032daf1843cd963e0cccfd16a3d7
Source dataset
uspto-grants-2008_07
Patent number
US07396487B2

Reaction notes

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