Azobisisobutyronitrile → Methyl 4'-(bromomethyl)biphenyl-2-carboxylate

HRID 487998Notes

Reaction equation

HRID 487998 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:17]=[CH:16][CH:15]=[CH:14][C:9]=2[C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=1.[Br:18]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:18][CH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:17]=[CH:16][CH:15]=[CH:14][C:9]=2[C:10]([O:12][CH3:13])=[O:11])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 1393873(1,1'-Biphenyl)-2-carboxylic acid, 4'-methyl-, methyl ester

Product 1

HCID 11012181Methyl 4'-(bromomethyl)biphenyl-2-carboxylate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

2.0 g of methyl 2-(4-methylphenyl)benzoate, 1.6 g of N-bromosuccinimide and 0.05 g of α,α'-azobis(isobutyronitrile) were heated in 110 ml of carbon tetrachloride under reflux for 2 hr. The succinimide was filtered off. The filtrate was concentrated, and the residue was recrystallized from a mixed solvent of n-hexane-isopropyl ether to prepare 1.6 g of the title compound.

Workup

  1. temperatureunder reflux for 2 hr
  2. filtrationThe succinimide was filtered off
  3. concentrationThe filtrate was concentrated
  4. customthe residue was recrystallized from a mixed solvent of n-hexane-isopropyl ether
  5. customto prepare 1.6 g of the title compound

Sources & evidence

ORD record
ord-8e344c4356c54b17b353f90da6025ced
Source dataset
uspto-grants-1994_03
Patent number
US05298518

Reaction notes

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