Water → tert-Butyl(2,5-difluorophenoxy)dimethylsilane

HRID 1418481Notes

Reaction equation

HRID 1418481 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[OH:9].[H-].[Na+].[Si:12](Cl)([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13].O>CN(C=O)C>[Si:12]([O:9][C:3]1[CH:4]=[C:5]([F:8])[CH:6]=[CH:7][C:2]=1[F:1])([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 28928tert-Butyldimethylsilyl chlorideHCID 949522,5-Difluorophenol

Product 1

HCID 11230299tert-Butyl(2,5-difluorophenoxy)dimethylsilaneYield 94,020.297%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 2,5-difluorophenol (15.1 g, 116 mmol) in DMF (100 ml) was added sodium hydride (60% W/W dispersion in mineral oil; 5.13 g, 139 mmol) with ice-cooling. After stirring for 30 min, tert-butyldimethylsilyl chloride (17.5 g, 0.116 mmol) was added and stirring was continued for an additional 1 hr. The mixture was poured into water (200 ml) and extracted with ether (300 ml). The extract was washed with brine (200 ml), dried (sodium sulfate) and solvent removed by evaporation to give 26.65 g (94%) of the titled compound as a colorless oil.

Workup

  1. temperaturecooling
  2. stirringstirring
  3. waitwas continued for an additional 1 hr
  4. extractionextracted with ether (300 ml)
  5. washThe extract was washed with brine (200 ml)
  6. dry with materialdried (sodium sulfate) and solvent
  7. customremoved by evaporation

Sources & evidence

ORD record
ord-8a193727f968428697e0a1e0a028939b
Source dataset
uspto-grants-1999_03
Patent number
US05883106

Reaction notes

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