2,4,5-Trichlorotoluene → 1-(Bromomethyl)-2,4,5-trichlorobenzene

HRID 1463285Notes

Reaction equation

HRID 1463285 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([Cl:9])=[CH:4][C:3]=1[CH3:10].[Br:11]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([Cl:9])=[CH:4][C:3]=1[CH2:10][Br:11]

Participants

4

Reactant 2

HCID 231282,4,5-TrichlorotolueneHCID 67184N-bromobutanimide

Product 1

HCID 139449891-(Bromomethyl)-2,4,5-trichlorobenzeneYield 80%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

Under a nitrogen atmosphere, a stirred solution of 5.0 grams (0.026 mole) of 2,4,5-trichlorotoluene and 5.3 grams (0.030 mole) of N-bromosuccinimide in 30 ml of carbon tetrachloride was heated to reflux and then was irradiated with a sun lamp during a 10 minute period. The reaction mixture was allowed to cool to ambient temperature at which time it was filtered to remove excess succinimide. The filtrate was concentrated under reduced pressure to a residual oil. The oil was distilled under vacuum, yielding four fractions in the boiling point range of 130°-152° C./5 mm Hg. NMR analysis of the fractions indicated that two fractions, boiling point 140°-150° C./5 mm Hg., contained the majority of the reaction product. The two fractions were combined and diluted with 1 ml of petroleum ether. The mixture was filtered to remove unreacted starting material. The filtrate was diluted with 12 ml of petroleum ether, and the solution was cooled in dry-ice. The solvent was removed from the resultant solid by pipette. The solid was dried under reduced pressure, yielding 2.7 grams of 80% pure 2,4,5-trichlorophenylmethyl bromide. The NMR spectrum was consistent with the proposed structure.

Workup

  1. temperatureto reflux
  2. customwas irradiated with a sun lamp during a 10 minute period
  3. filtrationwas filtered
  4. customto remove excess succinimide
  5. concentrationThe filtrate was concentrated under reduced pressure to a residual oil
  6. distillationThe oil was distilled under vacuum
  7. customyielding four fractions in the boiling point range of 130°-152° C./5 mm Hg
  8. filtrationThe mixture was filtered
  9. customto remove unreacted
  10. additionThe filtrate was diluted with 12 ml of petroleum ether
  11. temperaturethe solution was cooled in dry-ice
  12. customThe solvent was removed from the resultant solid by pipette
  13. customThe solid was dried under reduced pressure

Sources & evidence

ORD record
ord-e3cb0ecc26494634987d389af0d5e067
Source dataset
uspto-grants-1994_04
Patent number
US05300503

Reaction notes

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