Bromine → 2,4-Dibromo-6-bromomethylanisole

HRID 444100Notes

Reaction equation

HRID 444100 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([Br:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[O:10][CH3:11].[Br:12]Br>ClC(Cl)(Cl)Cl.C(OOCC1C=CC=CC=1)C1C=CC=CC=1>[Br:1][C:2]1[CH:7]=[C:6]([Br:8])[CH:5]=[C:4]([CH2:9][Br:12])[C:3]=1[O:10][CH3:11]

Participants

5

Reactant 2

HCID 24408BromineHCID 3465071,5-Dibromo-2-methoxy-3-methylbenzene

Product 1

HCID 205361872,4-Dibromo-6-bromomethylanisoleYield 71.5%

Reagents, catalysts & solvents 2

HCID 11229634Benzyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of the product of stage (b) (200 g) and benzyl peroxide (1 g) in tetrachloromethane (600 ml) was heated to reflux with stirring. Bromine (114 g) was added dropwise, and the mixture was stirred until it cooled to room temperature. Evaporation of the solvent gave an oil, distillation of which gave the title compound (183 g) as an oil, bp 115°-116° C./0.3 mm Hg.

Workup

  1. temperatureto reflux
  2. stirringthe mixture was stirred until it
  3. customEvaporation of the solvent
  4. customgave
  5. distillationan oil, distillation of which

Sources & evidence

ORD record
ord-9859723e10a2467ca6b64c6b4d7726df
Source dataset
uspto-grants-1981_04
Patent number
US04263037

Reaction notes

Loading…