Azobisisobutyronitrile → HCID 19988394, compound

HRID 973866Notes

Reaction equation

HRID 973866 reaction equation
[CH3:1][C:2]1[CH2:6][O:5][C:4](=[O:7])[C:3]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[Br:14]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N.C1(=O)NC(=O)CC1>C(Cl)(Cl)(Cl)Cl>[Br:14][CH:6]1[O:5][C:4](=[O:7])[C:3]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:2]1[CH3:1]

Participants

6

Reactant 4

HCID 6547AzobisisobutyronitrileHCID 11439SuccinimideHCID 67184N-bromobutanimideHCID 576159HCID 576159, compound

Product 1

HCID 19988394HCID 19988394, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

2,5-Dihydro-4-methyl-2-oxo-3-phenylfuran, (U.S. Pat. No. 3,622,569), (355 g) in carbon tetrachloride (50 mls) and N-bromosuccinimide (3.85 g) were heated under reflux in the presence of 2,2'-azobisisobutyronitrile (AIBN) (cat.quantity) and a 150W lamp. After 1 h a pale yellow solution was formed accompanied by the presence of succinimide. T.l.c. analysis showed a mixture of products. After filtration, and removal of solvent, the residue was purified by flash chroma-tography on silica gel eluting with 10% ethyl acetate/hexane. The title compound was obtained as a viscous yellow oil, (3.53 g, 68%), (Found; M+, 251.9802. C11H9O2Br requires M, 251.9786); νmax 1780(s) and 1650(w)cm-1 ; δH (CDCl3) 2.28 (3H,s), 6.80 (1H,s) and 7.45 (5H,m).

Workup

  1. customAfter 1 h a pale yellow solution was formed
  2. additiona mixture of products
  3. filtrationAfter filtration, and removal of solvent
  4. customthe residue was purified by flash chroma-tography on silica gel eluting with 10% ethyl acetate/hexane

Sources & evidence

ORD record
ord-9d00fa765c034acc8be349ec99891199
Source dataset
uspto-grants-1991_11
Patent number
US05064649

Reaction notes

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