N-bromobutanimide → 2-(Bromomethyl)-4-chloro-1-fluorobenzene

HRID 2058660Notes

Reaction equation

HRID 2058660 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([F:9])=[C:6]([CH3:8])[CH:7]=1.C1C(=O)N([Br:17])C(=O)C1>C(Cl)(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([F:9])=[C:6]([CH:7]=1)[CH2:8][Br:17]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 27251135-Chloro-2-fluorotoluene

Product 1

HCID 27736262-(Bromomethyl)-4-chloro-1-fluorobenzene

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 5-chloro-2-fluorotoluene (2.9 g; prepared by a modified Schiemann reaction on 4-chloro-2-methylaniline), NBS (3.6 g) benzoyl peroxide (100 mg) and carbon tetrachloride (25 ml) was refluxed 2h. The mixture was cooled, filtered and the solvent removed. Distillation gave 5-chloro-2-fluorobenzyl bromide (3 g), b.p. 104°/15 mm.

Workup

  1. temperaturewas refluxed 2h
  2. temperatureThe mixture was cooled
  3. filtrationfiltered
  4. customthe solvent removed
  5. distillationDistillation

Sources & evidence

ORD record
ord-7bd33f0403724bdc86fc45d7e27d9ca0
Source dataset
uspto-grants-1982_03
Patent number
US04318909

Reaction notes

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