Potassium Carbonate → [2-(2,5-Difluorophenoxy)ethoxy]triisopropylsilane

HRID 1712583Notes

Reaction equation

HRID 1712583 reaction equation
[F: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][CH2:18][O:19][Si:20]([CH:27]([CH3:29])[CH3:28])([CH:24]([CH3:26])[CH3:25])[CH:21]([CH3:23])[CH3:22]>CC(C)=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[O:9][CH2:17][CH2:18][O:19][Si:20]([CH:24]([CH3:25])[CH3:26])([CH:21]([CH3:23])[CH3:22])[CH:27]([CH3:28])[CH3:29]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 949522,5-DifluorophenolHCID 11450272(2-Iodoethoxy)triisopropylsilane

Product 1

HCID 67369881[2-(2,5-Difluorophenoxy)ethoxy]triisopropylsilane

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The stirred mixture of 0.80 g of 2,5-difluorophenol, 0.82 g of potassium carbonate, 1.98 g of (2-iodoethoxy)triisopropylsilane and 10 ml of acetone is kept at reflux over 3 hours. The reaction mixture is cooled, poured onto water (100 ml) and extracted with tert-butyl methyl ether (2×100 ml). The organic phases are washed with brine (1×80 ml) dried over sodium sulphate, filtered and concentrated by evaporation. The title compound is obtained as a colourless oil from the residue by means of flash chromatography (SiO2 60F). Rt=6.63.

Workup

  1. temperatureat reflux over 3 hours
  2. temperatureThe reaction mixture is cooled
  3. additionpoured onto water (100 ml)
  4. extractionextracted with tert-butyl methyl ether (2×100 ml)
  5. washThe organic phases are washed with brine (1×80 ml)
  6. dry with materialdried over sodium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-0e3987179f2d44f69da5850d824cfc1f
Source dataset
uspto-grants-2010_09
Patent number
US07790715B2

Reaction notes

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