N-bromobutanimide → 1-Bromo-3-(bromomethyl)-5-methylbenzene

HRID 1356791Notes

Reaction equation

HRID 1356791 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH3:9])[CH:5]=[C:6]([CH3:8])[CH:7]=1.[Br:10]N1C(=O)CCC1=O>C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C1C=CC=CC=1>[Br:1][C:2]1[CH:7]=[C:6]([CH:5]=[C:4]([CH3:9])[CH:3]=1)[CH2:8][Br:10]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 136357Benzene, 1-bromo-3,5-dimethyl-

Product 1

HCID 223242611-Bromo-3-(bromomethyl)-5-methylbenzeneYield 66.3%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 241BenzeneSolvent

Procedure

5-Bromo-m-xylene (10.0 g; 54.0 mmol), N-bromosuccinimide (9.63 g; 54.0 mmol), and benzoyl peroxide (150 mg) were added to benzene (100 ml), and the mixture was heated under reflux for 2.5 hours. The resultant mixture was left to cool to room temperature, and insoluble matter was filtered off, followed by washing with benzene. The filtrate was evaporated under reduced pressure, and the residue was taken up in n-hexane. The mixture was left to stand for 30 minutes, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:0→20:1), to thereby yield 9.44 g of the target compound (yield: 66.3%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2.5 hours
  3. filtrationinsoluble matter was filtered off
  4. washby washing with benzene
  5. customThe filtrate was evaporated under reduced pressure
  6. waitThe mixture was left
  7. dry with materialdried over magnesium sulfate
  8. customThe solvent was evaporated under reduced pressure
  9. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:0→20:1)

Sources & evidence

ORD record
ord-7ff0af5f47044640aeb0d0cc1383b1b3
Source dataset
uspto-grants-2003_07
Patent number
US06586633B1

Reaction notes

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