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

HRID 1013787Notes

Reaction equation

HRID 1013787 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[CH3:10].[Br:11]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:11][CH2:10][C:3]1[CH:4]=[CH:5][C:6]([O:8][CH3:9])=[CH:7][C:2]=1[Cl:1]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 69517572-Chloro-4-methoxytoluene

Product 1

HCID 223274281-(Bromomethyl)-2-chloro-4-methoxybenzeneYield 98%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

Heat a solution of 2-chloro-4-methoxy-1-methyl-benzene (2.0 g, 13 mmol), N-bromosuccinimide (2.7 g, 15 mmol), and benzoyl peroxide (50 mg) in CCl4 (50 mL) to reflux and stir for 3 hr. Cool the reaction to room temperature and quench with water. Extract the aqueous with CH2Cl2, dry over MgSO4, and filter. Remove the solvent to afford 3.0 g (98%) of the desired product.

Workup

  1. temperatureto reflux
  2. temperatureCool
  3. customthe reaction to room temperature
  4. customquench with water
  5. extractionExtract the aqueous with CH2Cl2
  6. dry with materialdry over MgSO4
  7. filtrationfilter
  8. customRemove the solvent

Sources & evidence

ORD record
ord-85d41720102947e3b40a0628ce0bb18d
Source dataset
uspto-grants-2011_07
Patent number
US07981918B2

Reaction notes

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