Bromine → 2,4-Dibromo-6-bromomethylanisole

HRID 1155975Notes

Reaction equation

HRID 1155975 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-3f6fa2b764034652902cc9d6b7539bec
Source dataset
uspto-grants-1982_06
Patent number
US04333759

Reaction notes

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