Benzoyl Peroxide → 4-(Bromomethyl)-1-chloro-2-methoxybenzene

HRID 1443225Notes

Reaction equation

HRID 1443225 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[O:9][CH3:10].[Br:11]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][Br:11])=[CH:4][C:3]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 993521-Chloro-2-methoxy-4-methylbenzene

Product 1

HCID 136628594-(Bromomethyl)-1-chloro-2-methoxybenzene

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
105 °C

Procedure

57 g (363.96 mmol) of 2-chloro-5-methylanisole is dissolved in 800 ml of carbon tetrachloride and mixed at room temperature with 69.9 g (393.08 mmol) of N-bromosuccinimide. After 174.6 mg of benzoyl peroxide is added, it is refluxed for five hours (bath temperature 105° C.). The reaction mixture is suctioned off via a glass fiber filter, rewashed, and the solution is spun in in a rotary evaporator. 83.6 g (97.5%) of the desired product (contains traces of starting material and dibromide), which is incorporated in crude form into the next stage, is obtained.

Workup

  1. filtrationfilter
  2. customthe solution is spun in in a rotary evaporator
  3. customis obtained

Sources & evidence

ORD record
ord-d4bab81ee2764dea9145afb30795451e
Source dataset
uspto-grants-2010_02
Patent number
US07659297B2

Reaction notes

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