Azobisisobutyronitrile → HCID 86632316, compound

HRID 1527894Notes

Reaction equation

HRID 1527894 reaction equation
[C:1]([O:5][C:6](=[O:23])[N:7]([C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[C:14]([Si:19]([CH3:22])([CH3:21])[CH3:20])[CH:13]=1)[Si:8]([CH3:11])([CH3:10])[CH3:9])([CH3:4])([CH3:3])[CH3:2].[Br:24]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[C:1]([O:5][C:6](=[O:23])[N:7]([C:12]1[CH:17]=[CH:16][C:15]([CH2:18][Br:24])=[C:14]([Si:19]([CH3:21])([CH3:20])[CH3:22])[CH:13]=1)[Si:8]([CH3:11])([CH3:9])[CH3:10])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 86632315HCID 86632315, compound

Product 1

HCID 86632316HCID 86632316, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A suspension of tert-butyl[4-methyl-3-(trimethylsilyl)phenyl](trimethylsilyl)carbamate (3.00 g, 8.55 mmol), N-bromosuccinimide (NBS, 1.59 g, 8.97 mmol), 2,2′-azobis(2-methylpropionitrile) (AIBN, 42 mg, 0.26 mmol) in CCl4 (40 mL) was refluxed under N2 for 16 h. The reaction mixture was cooled down; hexanes (100 mL) were added and the solid was filtered off and washed with EtOAc. The combined filtrate was washed with aq. NaHCO3, dried over Na2SO4, filtered, concentrated on rotavap and further dried under vacuum. This material was not purified but used directly in the next step (˜80%).

Workup

  1. temperaturewas refluxed under N2 for 16 h
  2. temperatureThe reaction mixture was cooled down
  3. filtrationthe solid was filtered off
  4. washwashed with EtOAc
  5. washThe combined filtrate was washed with aq. NaHCO3
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated on rotavap
  9. customfurther dried under vacuum
  10. customThis material was not purified

Sources & evidence

ORD record
ord-ca975aa060f040f483d2a3dd7979f3ba
Source dataset
uspto-grants-2015_07
Patent number
US09090561B2

Reaction notes

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