Triethylamine → (3-Bromophenoxy)(tert-butyl)dimethylsilane

HRID 741799Notes

Reaction equation

HRID 741799 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.CCN(CC)CC.[Si:16](Cl)([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([O:8][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 115633-BromophenolHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 11254705(3-Bromophenoxy)(tert-butyl)dimethylsilaneYield 96.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-bromophenol (50 g, 289 mmol) in 340 mL DMF was added Et3N (35 g, 347 mmol) and tert-butyldimethylsilyl chloride (52 g, 347 mmol). The mixture was stirred for 0.5 h, and then diluted with ET2O (2 L). The organic phase was washed with 5% aqueous HCl and brine, and dried over MgSO4. Flash chromatography using hexane:EtOAc (95:5) gave 80.1 g (96%) of product.

Workup

  1. additiondiluted with ET2O (2 L)
  2. washThe organic phase was washed with 5% aqueous HCl and brine
  3. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-7e2f6278f137414980b98cb3d9b17152
Source dataset
uspto-grants-1996_09
Patent number
US05552437

Reaction notes

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