N-bromobutanimide → 4-(Bromomethyl)-1-chloro-2-methoxybenzene

HRID 1934708Notes

Reaction equation

HRID 1934708 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>ClCCl>[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

4

Reactant 2

HCID 67184N-bromobutanimideHCID 993521-Chloro-2-methoxy-4-methylbenzene

Product 1

HCID 136628594-(Bromomethyl)-1-chloro-2-methoxybenzeneYield 23.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-chloro-3-methoxytoluene (5.65 g) and N-bromosuccinimide (6.74 g) in anhydrous dichloromethane (60 mL) was added 2,2′-azolbis(4-methoxy-2,4-diaethylvaleronitrile) (674 mg). After stirring for 3 hours under reflux, the mixture was washed with water and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was triturated with hexane to give 4-chloro-3-methoxybenzyl bromide as white powders (2.00 g).

Workup

  1. temperatureunder reflux
  2. washthe mixture was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was triturated with hexane

Sources & evidence

ORD record
ord-051df3d99384434b95b31548bbdf271c
Source dataset
uspto-grants-2002_05
Patent number
US06384080B1

Reaction notes

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