Azobisisobutyronitrile → HCID 11155397, compound

HRID 2227395Notes

Reaction equation

HRID 2227395 reaction equation
[C:1]([Si:5]([O:18][C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([CH3:26])[CH:20]=1)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)([CH3:4])([CH3:3])[CH3:2].[Br:27]N1C(=O)CCC1=O.CC(N=NC(C#N)(C)C)(C#N)C.CCCCCC>C(Cl)(Cl)(Cl)Cl>[C:1]([Si:5]([O:18][C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([CH2:26][Br:27])[CH:20]=1)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 6547AzobisisobutyronitrileHCID 8058HexaneHCID 67184N-bromobutanimideHCID 18473241HCID 18473241, compound

Product 1

HCID 11155397HCID 11155397, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

tert-Butyl(4-chloro-3-methylphenoxy)diphenylsilane (88.69 g, 0.233 mol), N-bromosuccinimide (49.8 g, 0.279 mol), and AIBN (3.82 g, 0.023 mol) were heated at reflux in CCl4 (500 mL) for 7 h. The reaction mixture was concentrated in vacuo, dissolved in 10% EtOAc/hexane, the succinimide filtered off, and the filtrate concentrated in vacuo to give a mixture of the mono- and di-bromides. Chromatography (SiO2)(100% hexane) gave the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutiondissolved in 10% EtOAc/hexane
  3. filtrationthe succinimide filtered off
  4. concentrationthe filtrate concentrated in vacuo
  5. customto give

Sources & evidence

ORD record
ord-eddca4edecdf4c76b4346e76d311e075
Source dataset
uspto-grants-2002_07
Patent number
US06413964B1

Reaction notes

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