Azobisisobutyronitrile → HCID 19741700, compound

HRID 2255124Notes

Reaction equation

HRID 2255124 reaction equation
[CH3:1][C:2]([Si:5]([CH3:19])([CH3:18])[O:6][C:7]1[CH:8]=[C:9]([CH:14]=[CH:15][C:16]=1[CH3:17])[C:10]([O:12][CH3:13])=[O:11])([CH3:4])[CH3:3].[Br:20]N1C(=O)CCC1=O.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[Br:20][CH2:17][C:16]1[CH:15]=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][C:7]=1[O:6][Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:18])[CH3:19]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 23282096HCID 23282096, compound

Product 1

HCID 19741700HCID 19741700, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of methyl 3-[(1,1-dimethylethyl)dimethylsilyl]oxy-4-methylbenzoate (11.36 g, 40.5 mmol) from Preparation 13, N-bromosuccinimide (6.5 g, 36.5 mmol), and AIBN 100 mg, 0.61 mmol) in CCl4. The reaction mixture is stirred at room temperature for 1 hour while exposed to a high intensity light bulb. The precipitate is removed by suction filtration and the filtrate is concentrated. The residue is purified by silica gel chromatography (1% tetrahydrofuran/petroleum ether). An oil of methyl 4-(bromomethyl)-3-[[(1,1-dimethylethyl)-dimethylsilyl]oxy]benzoate is obtained 99.87 g, 75%).

Workup

  1. customThe precipitate is removed by suction filtration
  2. concentrationthe filtrate is concentrated
  3. customThe residue is purified by silica gel chromatography (1% tetrahydrofuran/petroleum ether)

Sources & evidence

ORD record
ord-a4ad0e61d1eb414d917f71e06380f384
Source dataset
uspto-grants-1993_08
Patent number
US05238958

Reaction notes

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