Azobisisobutyronitrile → Methyl 4-bromomethyl-2-(4-fluorophenyl)benzoate

HRID 2228008Notes

Reaction equation

HRID 2228008 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:17]=[C:16]([CH3:18])[CH:15]=[CH:14][C:9]=2[C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=1.[Br:19]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>ClC(Cl)(Cl)Cl>[Br:19][CH2:18][C:16]1[CH:15]=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[CH:17]=1

Participants

6

Reactant 4

HCID 6547AzobisisobutyronitrileHCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 18474522Methyl 2-(4-fluorophenyl)-4-methylbenzoate

Product 1

HCID 18399506Methyl 4-bromomethyl-2-(4-fluorophenyl)benzoate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of methyl 2-(4-fluorophenyl)-4-methylbenzoate (54.18 g; 0.22 mol), N-bromosuccinimide (39.6 g; 0.22 mol), 2,2′-azobis(2′-methylproprionitrile) (0.25 g; 1.5 mmol) and benzoylperoxide (0.25 g; 1 mmol) in tetrachloromethane (550 ml) was heated at reflux for 6 hours. The solid was filtered and the filtrate evaporated to give methyl 4-bromomethyl-2-(4-fluorophenyl)benzoate as an oil (79.7 g; 79%) which was used in the next step without purification.

Workup

  1. temperatureat reflux for 6 hours
  2. filtrationThe solid was filtered
  3. customthe filtrate evaporated

Sources & evidence

ORD record
ord-9ae8ad8850bc4cbbb4f748aaba7e5d26
Source dataset
uspto-grants-2002_07
Patent number
US06414145B1

Reaction notes

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