Bromine → 1-Bromo-4-methoxy-2,5-dimethylbenzene

HRID 2416370Notes

Reaction equation

HRID 2416370 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[O:9][CH3:10].[Br:11]Br>C(Cl)(Cl)Cl.C(Cl)(Cl)(Cl)Cl>[Br:11][C:6]1[C:5]([CH3:8])=[CH:4][C:3]([O:9][CH3:10])=[C:2]([CH3:1])[CH:7]=1

Participants

5

Reactant 2

HCID 24408BromineHCID 743502,5-Dimethylanisole

Product 1

HCID 27525981-Bromo-4-methoxy-2,5-dimethylbenzeneYield 89%

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

In a three-neck flask, 60 g (4.4×10−1 mol) of 2,5-dimethylanisole was dissolved in 600 ml of CHCl3, and then cooled to 0° C. using ice bath. To the solution, 70.32 g (4.4×10−1 mol) of Br2 in 200 ml of CCl4 was added dropwise over 1 hour. While maintaining the reaction solution at 0° C., the reaction was left to stand for 7 hours. The reaction solution was washed 3 times with NaOH saturated solution and distilled under reduced pressure, to remove the solvent. The remaining liquid was vacuum-distilled, to produce the title compound in a liquid state. Yield: 89% (83.14 g).

Workup

  1. temperatureWhile maintaining the reaction solution at 0° C.
  2. waitthe reaction was left
  3. washThe reaction solution was washed 3 times with NaOH saturated solution
  4. distillationdistilled under reduced pressure
  5. customto remove the solvent
  6. distillationThe remaining liquid was vacuum-distilled

Sources & evidence

ORD record
ord-a3a24fbcc01b4152b8013403de572769
Source dataset
uspto-grants-2004_11
Patent number
US06824892B2

Reaction notes

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