Benzoyl Peroxide → 1-(Bromomethyl)-4-fluoro-2-nitrobenzene

HRID 1720029Notes

Reaction equation

HRID 1720029 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[Br:12]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][Br:12])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1

Participants

5

Reactant 3

HCID 7187Benzoyl Peroxide2×HCID 67184N-bromobutanimideHCID 679654-Fluoro-2-nitrotoluene

Product 1

HCID 127613791-(Bromomethyl)-4-fluoro-2-nitrobenzene

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a stirred solution of 4-fluoro-2-nitro toluene (48.9 g) and N-bromosuccinimide (56 g) in carbon tetrachloride (300 ml) was added benzoylperoxide (0.78 g). The mixture was heated under reflux for 90 minutes. Additionally, benzoylperoxide (0.78 g) was added to the mixture. Reflux was continued 90 minutes then, cooled to room temperature.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 90 minutes
  3. temperatureReflux

Sources & evidence

ORD record
ord-75f22451642547eba7d5a1a1f12a4943
Source dataset
uspto-grants-1996_04
Patent number
US05504095

Reaction notes

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