Azobisisobutyronitrile → tert-Butyl 3-(bromomethyl)benzoate

HRID 968872Notes

Reaction equation

HRID 968872 reaction equation
[C:1]([O:5][C:6](=[O:14])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH3:13])[CH:8]=1)([CH3:4])([CH3:3])[CH3:2].C1C(=O)N([Br:22])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[C:1]([O:5][C:6](=[O:14])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH2:13][Br:22])[CH:8]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 236097Tert-butyl 3-methylbenzoate

Product 1

HCID 14591193tert-Butyl 3-(bromomethyl)benzoate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

The crude 3-methyl-benzoic acid tert-butyl ester was reacted with NBS (0.31 g, 1.726 mmol), AIBN (0.28 g, 1.726 mmol) in CCl4 (30 mL) according to the procedure for the preparation of compound 55 in example 1. After separation by chromatography eluted with CHCl3—MeOH (50:1), a mixture of two products was obtained. One of them was the product (61% pure) with MS (ESI) 272.76 (M+H+). This mixture was not further separated and directly used in the next step reaction.

Workup

  1. customAfter separation by chromatography
  2. washeluted with CHCl3—MeOH (50:1)
  3. additiona mixture of two products
  4. customwas obtained
  5. customThis mixture was not further separated
  6. customdirectly used in the next step reaction

Sources & evidence

ORD record
ord-fe013c1478f84f05bd881be7c56902df
Source dataset
uspto-grants-2007_12
Patent number
US07304085B2

Reaction notes

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