Benzoyl Peroxide → 4-Bromo-3-(bromomethyl)benzonitrile

HRID 394557Notes

Reaction equation

HRID 394557 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[CH3:10].[Br:11]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[CH2:10][Br:11]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 27374944-Bromo-3-methylbenzonitrile

Product 1

HCID 114713444-Bromo-3-(bromomethyl)benzonitrileYield 36.4%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of of 4-bromo-3-methylbenzonitrile (1.0 g, 5.0 mmol) in carbon tetrachloride (7.5 mL) was added N-bromosuccinimide (1.0 g, 5.6 mmol) followed by of benzoylperoxide (50 mg 0.2 mmol) and the mixture was refluxed. After 10 hours, the reaction was cooled to rt, filtered, and the filtrate was washed with 10% NaHSO3 (5 mL) followed by water (5 mL). The organic layer was dried (Na2SO4), filtered, volatiles removed, and the residue was purified by flash chromatography on silica gel. Elution with 10% Ethyl acetate in hexanes gave the title compound (0.5 g, 36%) as a white solid. 1H NMR (270 MHz, CDCl3) δ4.55 (s, 2 H), 7.38-7.42 (m, 1 H), 7.65-7.77 (m, 2H).

Workup

  1. temperaturethe mixture was refluxed
  2. filtrationfiltered
  3. washthe filtrate was washed with 10% NaHSO3 (5 mL)
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. customvolatiles removed
  7. customthe residue was purified by flash chromatography on silica gel
  8. washElution with 10% Ethyl acetate in hexanes

Sources & evidence

ORD record
ord-b1dcae18242147b0a2866ad419e80c41
Source dataset
uspto-grants-2003_08
Patent number
US06602883B1

Reaction notes

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