N-bromobutanimide → 2-(Bromomethyl)-4-fluoro-1-nitrobenzene

HRID 561366Notes

Reaction equation

HRID 561366 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH3:8])[CH:7]=1.[Br:12]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[Br:12][CH2:8][C:6]1[CH:7]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=1[N+:9]([O-:11])=[O:10]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 949565-Fluoro-2-nitrotoluene

Product 1

HCID 105616432-(Bromomethyl)-4-fluoro-1-nitrobenzene

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

574 g (3.70 mol) of 5-fluoro-2-nitrotoluene and 659 g (3.70 mol) of N-bromosuccinimide were introduced into 3.7 l of chloroform, 30.0 g (183 mmol) of 2,2′-azobis-2-methylpropanenitrile were added, and the mixture was heated under reflux with irradiation by a UV lamp for 18 h. Cooling was followed by filtration with suction, and the filtrate was concentrated, the residue was taken up in diethyl ether and filtered with suction, and the filtrate was concentrated. The residue was dissolved in dichloromethane and petroleum ether and purified by flash chromatography (mobile phase: petroleum ether/ethyl acetate gradient) to result in 92.0 g (10% of theory) of the title compound.

Workup

  1. additionwere added
  2. temperaturethe mixture was heated
  3. temperatureunder reflux with irradiation by a UV lamp for 18 h
  4. temperatureCooling
  5. filtrationwas followed by filtration with suction
  6. concentrationthe filtrate was concentrated
  7. filtrationfiltered with suction
  8. concentrationthe filtrate was concentrated
  9. dissolutionThe residue was dissolved in dichloromethane
  10. custompetroleum ether and purified by flash chromatography (mobile phase: petroleum ether/ethyl acetate gradient)

Sources & evidence

ORD record
ord-cd736b99c98b4c18b7ffa8c98faa9494
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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