Azobisisobutyronitrile → HCID 86725422, compound
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](=[O:11])[CH3:10])=[CH:4][CH:3]=1.[Br:12]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:12][CH:8]([C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=1)[C:9](=[O:11])[CH3:10]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
A solution of 1-(4-bromophenyl)propan-2-one (1.173 mmol) in carbon tetrachloride (2.5 mL) was degassed with a stream of nitrogen for five minutes, at which point the solution was treated with N-bromosuccinimide (1.291 mmol) and azobisisobutyronitrile (0.059 mmol). The reaction vessel was purged with nitrogen and sealed, and the mixture was heated overnight at 80° C. with stirring. The resulting orange solution was concentrated to dryness in vacuo. Purification of the crude material by silica gel chromatography (0-35% ethyl acetate/hexanes) afforded the title compound (94 mg, 19%). 1H NMR (400 MHz, DMSO-d6) d ppm 2.27 (s, 3 H) 6.12 (s, 1 H) 7.39 (m, J=8.59 Hz, 2 H) 7.62 (d, J=8.59 Hz, 2 H).
Workup
- customThe reaction vessel was purged with nitrogen
- customsealed
- concentrationThe resulting orange solution was concentrated to dryness in vacuo
- customPurification of the crude material by silica gel chromatography (0-35% ethyl acetate/hexanes)
Sources & evidence
- ORD record
- ord-2352023915da44e1932344a5f9d6c1b0
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09084794B2
Reaction notes
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