Azobisisobutyronitrile → Methyl 2-(bromomethyl)benzoate

HRID 1429377Notes

Reaction equation

HRID 1429377 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C1C(=O)N([Br:19])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl.O>[Br:19][CH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

6

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 33094Methyl o-toluateHCID 67184N-bromobutanimide

Product 1

HCID 2734813Methyl 2-(bromomethyl)benzoateYield 80%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of compound 18b (4.5 g, 30 mmol), NBS (5.9 g, 33 mmol) and AIBN (0.5 g, 3 mmol) in CCl4 (20 mL) was refluxed overnight. The mixture was taken up in H2O (20 mL) and extracted with DCM (100 mL). The organic layer was washed with brine, dried over Na2SO4, filtered and concentrated. The crude product was purified by CC to give the compound 18c (5.5 g, 80% yield).

Workup

  1. extractionextracted with DCM (100 mL)
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by CC

Sources & evidence

ORD record
ord-4e46a084462c423d84eb60f223fea357
Source dataset
uspto-grants-2015_01
Patent number
US08940722B2

Reaction notes

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