Benzoyl Peroxide → Methyl 4'-(bromomethyl)biphenyl-2-carboxylate

HRID 2210807Notes

Reaction equation

HRID 2210807 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:14]([O:16][CH3:17])=[O:15])=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1.[Br:18]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>ClC(Cl)(Cl)Cl>[Br:18][CH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:14]([O:16][CH3:17])=[O:15])=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 1393873(1,1'-Biphenyl)-2-carboxylic acid, 4'-methyl-, methyl ester

Product 1

HCID 11012181Methyl 4'-(bromomethyl)biphenyl-2-carboxylateYield 100%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

2.3 g of methyl 4'-methyl-(1, 1'-biphenyl)-2-carboxylate was dissolved in 900 ml of tetrachloromethane under a nitrogen flow. Then there were added 17.8 g of 1-bromo-2,5-pyrrolidinedione and a catalytic amount of dibenzoyl peroxide. After stirring for 2.5 hours at reflux temperature under a nitrogen atmosphere, the reaction mixture was cooled and filtered. The flitrate was evaporated, yielding >30 g (100% ) of methyl 4'-(bromomethyl)[1,1'-biphenyl]-2-carboxylate as a crude residue (interm. 36).

Workup

  1. temperatureat reflux temperature under a nitrogen atmosphere
  2. temperaturethe reaction mixture was cooled
  3. filtrationfiltered
  4. customThe flitrate was evaporated

Sources & evidence

ORD record
ord-dd807ed8ebd74f99885aa7881c817a34
Source dataset
uspto-grants-1995_10
Patent number
US05461050

Reaction notes

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