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

HRID 1935604Notes

Reaction equation

HRID 1935604 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) δ 4.55 (s, 2H), 7.38-7.42 (m, 1H), 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-6ccc8340927e4c34992af6af02bf417d
Source dataset
uspto-grants-2002_05
Patent number
US06387926B1

Reaction notes

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