Benzoyl Peroxide → 1-Bromo-2-(bromomethyl)-4-nitrobenzene

HRID 1256095Notes

Reaction equation

HRID 1256095 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[CH3:11].C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C1C(=O)N([Br:37])C(=O)C1>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[CH2:11][Br:37]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 2516721-Bromo-2-methyl-4-nitrobenzene

Product 1

HCID 109025011-Bromo-2-(bromomethyl)-4-nitrobenzeneYield 73%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 1-bromo-2-methyl-4-nitrobenzene (15 g, 79 mmol), benzoyl peroxide (2 g, 8 mmol) and NBS (17 g, 95 mmol) in CCl4 (150 mL) was stirred at reflux overnight. The mixture was cooled to room temperature and filtered, the filtrate was washed with water twice, dried over Na2SO4 and concentrated to give 1-bromo-2-(bromomethyl)-4-nitrobenzene as light yellow oil (17 g, 69%). 1H NMR: 400 MHz CDCl3 δ 8.37-8.34 (m, 1H), 8.05-8.02 (m, 1H), 7.77-7.75 (m, 1H), 3.87 (s, 2H).

Workup

  1. temperatureat reflux overnight
  2. filtrationfiltered
  3. washthe filtrate was washed with water twice
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2a2b125d622d4ca4bd5773e6e382a5c7
Source dataset
uspto-grants-2013_06
Patent number
US08461134B2

Reaction notes

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