Azobisisobutyronitrile → 2-(Bromomethyl)-6-methylphenylboronic acid

HRID 1097181Notes

Reaction equation

HRID 1097181 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[B:9]([OH:11])[OH:10].C1C(=O)N([Br:19])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[Br:19][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[B:9]([OH:10])[OH:11]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 5833222,6-Dimethylphenylboronic acid

Product 1

HCID 595941852-(Bromomethyl)-6-methylphenylboronic acid

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

2,6-dimethylphenylboronic acid (2.22 g, 14.8 mmol), NBS (1.31 g, 7.36 mmol, 0.5 eq) and AIBN (0.17 g, 1.0 mmol. 0.07 eq) were heated in refluxing CCl4 for 2 hours. The solution was allowed to cool then filtered. The solution was then washed with water (50 mL), dried over Na2SO4 and the solvent evaporated in vacuo. The resulting white powder (1.66 g) was ˜84% pure by HPLC and contained starting material and some di-brominated product. Column chromatography on silica gel 60 (elution conditions 0%-2% methanol in dichloromethane) failed to improve the purity and the crude material was used for the next step.

Workup

  1. temperatureto cool
  2. filtrationthen filtered
  3. washThe solution was then washed with water (50 mL)
  4. dry with materialdried over Na2SO4
  5. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-c446e21949284b9296701ec0b78a79f7
Source dataset
uspto-grants-2012_03
Patent number
US08143068B2

Reaction notes

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