O-Cresol → tert-Butyl-dimethyl-o-tolyloxy-silane

HRID 736033Notes

Reaction equation

HRID 736033 reaction equation
[CH3:1][C:2]([Si:5](Cl)([CH3:7])[CH3:6])([CH3:4])[CH3:3].[C:9]1([CH3:16])[C:14]([OH:15])=[CH:13][CH:12]=[CH:11][CH:10]=1.N1C=CN=C1.O>CN(C=O)C>[CH3:1][C:2]([Si:5]([CH3:7])([CH3:6])[O:15][C:14]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH3:16])([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 335O-CresolHCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 11310617tert-Butyl-dimethyl-o-tolyloxy-silane

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Add TBDMSCl (4.6 g, 30.5 mmol) to a solution of o-cresol (3 g, 28 mmol) and imidazole (2.08 g, 30.5 mmol) in 25 ml of dry DMF and stir at room temperature. After 7 h, pour the reaction into H2O and extract with hexane twice. Combine the organic layers, wash with H2O, dry over Na2SO4, filter and concentrate under reduced pressure to give a residue. Purify the residue by column chromatography on silica gel eluting with hexane to afford pure (1,1-dimethylethyl)dimethyl(2-methylphenoxy)silane as colourless oil. Add AIBN (330 mg, 1.98 mmol) to a solution of NBS (3.87 g, 21.76 mmol) and (1,1-dimethylethyl)dimethyl(2-methylphenoxy)silane (4.4 g, 19.78 mmol) in 100 ml of CCl4 and stir at reflux for 6 h. Concentrate the solvent under reduced pressure, add hexane and filter the solid. Wash the hexane with a saturated aqueous solution of NaHCO3 and H2O. Dry the organic phase over Na2SO4, filter and concentrate under reduced pressure to obtain [2-(bromomethyl)phenoxy](1,1-dimethylethyl)dimethylsilane as colourless oil.

Workup

  1. additionpour
  2. extractionextract with hexane twice
  3. washwash with H2O
  4. dry with materialdry over Na2SO4
  5. filtrationfilter
  6. concentrationconcentrate under reduced pressure
  7. customto give a residue
  8. customPurify the residue by column chromatography on silica gel eluting with hexane

Sources & evidence

ORD record
ord-4d34d12b2d8748d59584574181e1e519
Source dataset
uspto-grants-2009_09
Patent number
US07595315B2

Reaction notes

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