Benzoyl Peroxide → 2-(Bromomethyl)-1-chloro-3-methoxybenzene

HRID 1971447Notes

Reaction equation

HRID 1971447 reaction equation
[Cl:1][C:2]1[C:3]([CH3:10])=[C:4]([O:8][CH3:9])[CH:5]=[CH:6][CH:7]=1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[Br:29]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[C:3]=1[CH2:10][Br:29]

Participants

5

Reactant 3

HCID 7187Benzoyl Peroxide2×HCID 67184N-bromobutanimideHCID 767493-Chloro-2-methylanisole

Product 1

HCID 223274432-(Bromomethyl)-1-chloro-3-methoxybenzene

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To 13.0 g (84.92 mmol) 3-chloro-2-methylanisole in 80 ml CCl4 at reflux were added 0.4 g dibenzoyl peroxide and then, subsequently and portion-wise, a mixture of 15.2 g N-bromosuccinimide and 0.4 g dibenzoyl peroxide. After completion of reaction the mixture was evaporation-concentrated, the residue was dissolved in dichloromethane, was sequentially washed with water and saturated NaCl solution, was dried over MgSO4, was filtered and again evaporation-concentrated. 20.8 yellow oil.

Workup

  1. customAfter completion of reaction the mixture
  2. concentrationwas evaporation-concentrated
  3. dissolutionthe residue was dissolved in dichloromethane
  4. washwas sequentially washed with water and saturated NaCl solution
  5. dry with materialwas dried over MgSO4
  6. filtrationwas filtered
  7. concentrationagain evaporation-concentrated

Sources & evidence

ORD record
ord-34b1049013cf41cab7c3fa6fd23cd352
Source dataset
uspto-grants-2013_04
Patent number
US08431604B2

Reaction notes

Loading…