Azobisisobutyronitrile → Methyl 3-bromomethyl-5-phenylbenzoate

HRID 2228020Notes

Reaction equation

HRID 2228020 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[Br:18]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>>[Br:18][CH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

5

Reactant 4

HCID 6547AzobisisobutyronitrileHCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 11379139Methyl 3-methyl-5-phenylbenzoate

Product 1

HCID 18474535Methyl 3-bromomethyl-5-phenylbenzoateYield 80%

Procedure

A solution of methyl 3-methyl-5-phenylbenzoate (3.5 g; 15.6 mmol); N-bromosuccinimide (2.78 g; 15.6 mmol), 2,2′-azobis(2′-methylpropionitrile) (0.12 g; 0.72 mmol) and benzoylperoxide (0.12 g; 0.48 mmol) in tetrachloroamethane (120 ml) was heated at reflux for 5 hours. After evaporation to dryness, the residue was purified by flash chromatography eluting with petroleum ether/ethyl acetate (97/3) to give methyl 3-bromomethyl-5-phenylbenzoate as a solid. Yield=80%.

Workup

  1. temperatureat reflux for 5 hours
  2. customAfter evaporation to dryness
  3. customthe residue was purified by flash chromatography
  4. washeluting with petroleum ether/ethyl acetate (97/3)

Sources & evidence

ORD record
ord-99d62e40e6e74a66bba371b6ed068a51
Source dataset
uspto-grants-2002_07
Patent number
US06414145B1

Reaction notes

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