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Azobisisobutyronitrile → Methyl 4-bromomethyl-2-phenylbenzoate

HRID 2227990
Notes
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Reaction equation

HRID 2227990 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:3]=1.[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>C(Cl)(Cl)(Cl)Cl>[Br:18][CH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6547AzobisisobutyronitrileHCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 18474515HCID 18474515, compound

Product 1

HCID 18474540Methyl 4-bromomethyl-2-phenylbenzoate

Reagents, catalysts & solvents 1

HCID 5943
Carbon Tetrachloride
Solvent

Procedure

A solution of product from step C, (9.5 g; 42 mmol), N-bromosuccinimide (NBS) (8.22 g; 46.2 mmol), 2,2′-azobis(2′-methylpropionitrile) (25 mg; 0.15 mmol) and benzoylperoxide (25 mg; 0.1 mmol) in CCl4 (100 ml) was heated at reflux for 5 hours. The solid was filtered and the filtrate evaporated to give methyl 4-bromomethyl-2-phenylbenzoate as an oil (9.43 g; 74%) which was used in the next step without further purification.

Workup

  1. temperatureat reflux for 5 hours
  2. filtrationThe solid was filtered
  3. customthe filtrate evaporated

Sources & evidence

ORD record
ord-343efa2c2c1b47b28c6af57c1846fe02
Source dataset
uspto-grants-2002_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06414145B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes