Benzoyl Peroxide → 1-(Bromomethyl)-2-fluoro-3-nitrobenzene

HRID 2061121Notes

Reaction equation

HRID 2061121 reaction equation
C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[F:19][C:20]1[C:25]([N+:26]([O-:28])=[O:27])=[CH:24][CH:23]=[CH:22][C:21]=1[CH3:29].[Br:30]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:30][CH2:29][C:21]1[CH:22]=[CH:23][CH:24]=[C:25]([N+:26]([O-:28])=[O:27])[C:20]=1[F:19]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 134709572-Fluoro-1-methyl-3-nitrobenzene

Product 1

HCID 591391511-(Bromomethyl)-2-fluoro-3-nitrobenzeneYield 66.7%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

Benzoyl peroxide (10.7 g, 44 mmol) was added under reflux under nitrogen atmosphere to a solution of 2-fluoro-1-methyl-3-nitrobenzene (compound 2a-1) (68.2 g, 440 mmol) and N-bromosuccinimide (95.0 g, 528 mmol) in carbon tetrachloride (1500 mL), and the mixture was stirred under reflux for 5 hours. Impurities were then removed by filtration, and a crude product was obtained by vacuum concentration. It was then purified by column chromatography (hexane), and the title compound (68.7 g, 65%) was obtained as a yellow to light brown oil.

Workup

  1. temperatureunder reflux for 5 hours
  2. customImpurities were then removed by filtration
  3. customa crude product was obtained by vacuum concentration
  4. customIt was then purified by column chromatography (hexane)

Sources & evidence

ORD record
ord-4973eb0724694f1fb9ee5532066fa8ea
Source dataset
uspto-grants-2012_10
Patent number
US08278465B2

Reaction notes

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