Azobisisobutyronitrile → [2-(Bromomethyl)phenoxy](tert-butyl)dimethylsilane
Reaction equation
CC(N=NC(C#N)(C)C)(C#N)C.C1C(=O)N([Br:20])C(=O)C1.[CH3:21][C:22]([Si:25]([CH3:35])([CH3:34])[O:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[CH3:33])([CH3:24])[CH3:23]>C(Cl)(Cl)(Cl)Cl>[Br:20][CH2:33][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=1[O:26][Si:25]([C:22]([CH3:21])([CH3:23])[CH3:24])([CH3:34])[CH3:35]Participants
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
- temperatureat reflux for 6 h
- concentrationConcentrate the solvent under reduced pressure
- additionadd hexane
- filtrationfilter the solid
- washWash the hexane with a saturated aqueous solution of NaHCO3 and H2O
- dry with materialDry the organic phase over Na2SO4
- filtrationfilter
- concentrationconcentrate under reduced pressure
Sources & evidence
- ORD record
- ord-9beeeac70f6649f2a8d8c2f28bb1e971
- Source dataset
- uspto-grants-2009_09
- Patent number
- US07595315B2
Reaction notes
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