Benzoyl Peroxide → 4-(4-Bromomethylphenyl)butyl tert-butyldimethylsilyl ether

HRID 1751857Notes

Reaction equation

HRID 1751857 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Br:20]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Si:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:14]=[CH:15][C:16]([CH2:19][Br:20])=[CH:17][CH:18]=1)([C:4]([CH3:6])([CH3:5])[CH3:7])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 596786264-(4-Methylphenyl)butyl tert-butyldimethylsilyl ether

Product 1

HCID 596786244-(4-Bromomethylphenyl)butyl tert-butyldimethylsilyl ether

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a 50 ml round bottom flask is added 4-(4-methylphenyl)butyl tert-butyldimethylsilyl ether (0.25 g, 0.89 mmol), N-bromosuccinimide (0.158 g, 0.89 mmol), benzoyl peroxide (2.17 mg, 0.0089 mmol) and 10 ml carbon tetrachloride. This mixture is refluxed overnight after which it is cooled and filtered. The filtrate is concentrated and the resulting crude residue is purified by flash chromatography in ethyl acetate-hexanes to afford the product.

Workup

  1. temperatureThis mixture is refluxed overnight after which it
  2. temperatureis cooled
  3. filtrationfiltered
  4. concentrationThe filtrate is concentrated
  5. customthe resulting crude residue is purified by flash chromatography in ethyl acetate-hexanes
  6. customto afford the product

Sources & evidence

ORD record
ord-75149d28006b43838ed262c41c52d579
Source dataset
uspto-grants-2015_10
Patent number
US09161997B2

Reaction notes

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