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

HRID 657339Notes

Reaction equation

HRID 657339 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[CH:3]=1.C1C(=O)N([Br:17])C(=O)C1>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH2:9][Br:17])[CH:3]=1

Participants

4

Reactant 2

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

Product 1

HCID 223242611-Bromo-3-(bromomethyl)-5-methylbenzeneYield 112.3%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 1-bromo-3,5-dimethylbenzene (25.0 g, 135 mmol), NBS (24.0 g, 135 mmol) and BPO (1.30 g) in CCl4 (250 mL) was refluxed for 6 h. After cooling to room temperature, the mixture was filtered, and the filtrate was washed successively with saturated sodium bicarbonate (100 mL), water (2×50 mL) and brine (2×50 mL). The combined organic phases were dried (Na2SO4) and concentrated in vacuum to give 40.0 g of crude product 1-bromo-3-(bromomethyl)-5-methylbenzene.

Workup

  1. temperaturewas refluxed for 6 h
  2. filtrationthe mixture was filtered
  3. washthe filtrate was washed successively with saturated sodium bicarbonate (100 mL), water (2×50 mL) and brine (2×50 mL)
  4. dry with materialThe combined organic phases were dried (Na2SO4)
  5. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-57e359ec81a04a2999b9ab9376b73f09
Source dataset
uspto-grants-2011_12
Patent number
US08071588B2

Reaction notes

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