3-Acetylbenzonitrile → 3-(2-Bromoacetyl)benzonitrile

HRID 1736429Notes

Reaction equation

HRID 1736429 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[C:7]#[N:8])(=[O:3])[CH3:2].[Br:12]C1(Br)C(=O)NC(=O)NC1=O>C(OCC)C>[Br:12][CH2:2][C:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[C:7]#[N:8])=[O:3]

Participants

4

Reactant 2

HCID 802223-AcetylbenzonitrileHCID 948775,5-Dibromobarbituric acid

Product 1

HCID 27358673-(2-Bromoacetyl)benzonitrileYield 162.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 1.02 g (7.04 mmol) of 3-acetylbenzonitrile in 70 mL of ethylether was added 1.02 g (3.52 mmol, 0.5 equiv) of dibromobarbituric acid. The mixture was allowed to stir at room temperature overnight. The resultant white slurry was filtered and the filtrate was concentrated. Purification by flash chromotography (silica gel, 20% ethyl acetate/hexane) gave 1.28 g (81%) of the title compound as a whim solid: 1H NMR (400 MHz, CDCl3) δ8.26 (t, 1H, J=1.4 Hz), 8.20 (td, 1H, J=1.5, 8.0 Hz), 7.87 (dd, 1H, J=1.3, 7.8 Hz), 7.64 (t, 1H, J=7.9 Hz), 4.40 (s, 2H).

Workup

  1. filtrationThe resultant white slurry was filtered
  2. concentrationthe filtrate was concentrated
  3. customPurification by flash chromotography (silica gel, 20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-ad3673825cb74a35b8bdd3d6a35a7ccf
Source dataset
uspto-grants-1996_07
Patent number
US05541197

Reaction notes

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