Benzoyl Peroxide → 4-(Benzhydrylidene-amino)-3-bromomethyl-benzonitrile

HRID 2755

Reaction equation

HRID 2755 reaction equation
[C:1](=[N:14][C:15]1[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][C:16]=1[CH3:23])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:24]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl.C(Cl)Cl>[C:1](=[N:14][C:15]1[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][C:16]=1[CH2:23][Br:24])([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 193509624-(Benzhydrylidene-amino)-3-methyl-benzonitrile

Product 1

HCID 104996864-(Benzhydrylidene-amino)-3-bromomethyl-benzonitrileYield 56.9%

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(benzhydrylidene-amino)-3-methyl-benzonitrile (1.36 g, 4.27 mmol) in 40 mL of CCl4 is added N-bromosuccinimide (0.84 g, 4.7 mmol) and benzoyl peroxide (0.22 g, 0.64 mmol). The solution is heated to reflux for 16 h. The solution is cooled to ambient temperatures. The solution is diluted with CH2Cl2. The solution is washed with 1N NaOH and saturated NaCl. The organic layer is dried over MgSO4, filtered and concentrated. The crude material is purified by column chromatography eluting with a gradient of 5% EtOAc/hexanes to 10% EtOAc/hexanes. The title compound (0.91 g, 2.43 mmol) is obtained as an oil.

Workup

  1. temperatureThe solution is heated
  2. temperatureto reflux for 16 h
  3. temperatureThe solution is cooled to ambient temperatures
  4. washThe solution is washed with 1N NaOH and saturated NaCl
  5. dry with materialThe organic layer is dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude material is purified by column chromatography
  9. washeluting with a gradient of 5% EtOAc/hexanes to 10% EtOAc/hexanes

Sources & evidence

ORD record
ord-d5d7a05761ee49b4bed0ffdf724b4bc7
Source dataset
uspto-grants-1998_03
Patent number
US05731315

Linked notes

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