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

HRID 851513Notes

Reaction equation

HRID 851513 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:5]=1[CH3:11])([O-:3])=[O:2].[Br:12]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[N+:1]([C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:5]=1[CH2:11][Br:12])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 679654-Fluoro-2-nitrotoluene

Product 1

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

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 2-nitro-4-fluorotoluene (1.65 g), N-bromo-succinimide (1.78 g), carbon tetrachloride 10.0 ml) and benzoyl peroxide (0.1 g) was heated at the reflux temperature until the solid residue was observed to be floating at the surface (ca. 3 hours). After removing the solid by filtration, the filtrate was diluted with diethyl ether, washed with water, dried over anhydrous magnesium sulphate and concentrated by evaporation of the solvents under reduced pressure. The residue (estimated to contain ca. 35% w/w of the benzyl bromide in admixture with unchanged starting material) was subjected to column chromatography using a silica column and diethyl ether/petroleum ether (ratio 1:9 v/v) as eluent to yield pure 2-nitro-4-fluorobenzyl bromide.

Workup

  1. temperaturewas heated at the reflux temperature until the solid residue
  2. customto be floating at the surface (ca. 3 hours)
  3. customAfter removing the solid
  4. filtrationby filtration
  5. additionthe filtrate was diluted with diethyl ether
  6. washwashed with water
  7. dry with materialdried over anhydrous magnesium sulphate
  8. concentrationconcentrated by evaporation of the solvents under reduced pressure

Sources & evidence

ORD record
ord-74ebfe40f95c4b5ab96068132f0d2dda
Source dataset
uspto-grants-1983_05
Patent number
US04385070

Reaction notes

Loading…