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

HRID 863808Notes

Reaction equation

HRID 863808 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 mL of ethyl ether 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 tiltrate was concentrated. Purification by flash chromotography (silica gel, ethyl acetate/hexane) gave 1.28 g (81%) of the title compound as a white solid: 1H NMR (400 MHz, CDCl3) δ 8.26 (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 tiltrate was concentrated
  3. customPurification by flash chromotography (silica gel, ethyl acetate/hexane)

Sources & evidence

ORD record
ord-3b2f3b382b664ad78a072d441998cb56
Source dataset
uspto-grants-1996_10
Patent number
US05561142

Reaction notes

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