N-bromobutanimide → 3-Bromo-2-(bromomethyl)benzonitrile
Reaction equation
C1C(=O)N([Br:8])C(=O)C1.[Br:9][C:10]1[C:11]([CH3:18])=[C:12]([CH:15]=[CH:16][CH:17]=1)[C:13]#[N:14]>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:9][C:10]1[C:11]([CH2:18][Br:8])=[C:12]([CH:15]=[CH:16][CH:17]=1)[C:13]#[N:14]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
A mixture of NBS (3.45 g), dibenzoyl peroxide (100 mg) and 3-bromo-2-methylbenzonitrile (3.47 g) in carbon tetrachloride (40 ml) was heated at reflux under nitrogen for 48 h. The mixture was then cooled to room temperature, filtered and concentrated in vacuo to give a pale yellow solid. Chromatography eluting with dichloromethane gave the title compound as a white solid (4.23 g) m.p. 90°-93° C.
Workup
- temperaturewas heated
- temperatureat reflux under nitrogen for 48 h
- filtrationfiltered
- concentrationconcentrated in vacuo
- customto give a pale yellow solid
- washChromatography eluting with dichloromethane
Sources & evidence
- ORD record
- ord-0dcdab110f0f46959854301c623b7893
- Source dataset
- uspto-grants-1994_12
- Patent number
- US05374646
Reaction notes
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