Benzoyl Peroxide → 2-(Benzhydrylideneamino)-4-bromomethylbenzonitrile

HRID 1432857Notes

Reaction equation

HRID 1432857 reaction equation
[C:1](=[N:14][C:15]1[CH:22]=[C:21]([CH3:23])[CH:20]=[CH:19][C:16]=1[C:17]#[N:18])([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:1](=[N:14][C:15]1[CH:22]=[C:21]([CH2:23][Br:24])[CH:20]=[CH:19][C:16]=1[C:17]#[N:18])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 179851672-(Benzhydrylideneamino)-4-methylbenzonitrile

Product 1

HCID 179851902-(Benzhydrylideneamino)-4-bromomethylbenzonitrile

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 2-(benzhydrylidene-amino)-4-methyl-benzonitrile (11.2 g, 37.8 mmol) in 500 mL of CCl4 is added N-bromosuccinimide (7.06 g, 39.7 mmol), and benzoyl peroxide (0.92 g, 3.8 mmol). The solution is heated to reflux for 16 hours. After this time, the solution is filtered and the organic solution is concentrated under vacuum. The residue is purified by column chromatography eluting with a gradient of 20% t-butyl ether/hexanes to 25% t-butyl ether/hexanes. The product is obtained as an oil containing a mixture of the desired monobromide, dibromide and unreacted starting material. The mixture is assayed by proton NMR and is found to have a purity between 60-75%. 1H NMR (CDCl3, 300 MHz) δ7.82 (m, 2H), 7.42 (m, 9H), 6.92 (d, 1H), 6.81 (s, 1H), 4.29 (s, 2H).

Workup

  1. temperatureThe solution is heated
  2. temperatureto reflux for 16 hours
  3. filtrationAfter this time, the solution is filtered
  4. concentrationthe organic solution is concentrated under vacuum
  5. customThe residue is purified by column chromatography
  6. washeluting with a gradient of 20% t-butyl ether/hexanes to 25% t-butyl ether/hexanes
  7. customThe product is obtained as an oil
  8. additioncontaining

Sources & evidence

ORD record
ord-04a73c48cbcc4d5da6bcd7ab5f6682cc
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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