Azobisisobutyronitrile → HCID 66778012, compound

HRID 2091041Notes

Reaction equation

HRID 2091041 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]([O:12][CH3:13])=[O:11])=[C:7]([CH3:14])[C:6]=2[CH:15]=1.[Br:16]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(#N)C>[Br:16][CH2:14][C:7]1[C:6]2[CH:15]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=2[O:9][C:8]=1[C:10]([O:12][CH3:13])=[O:11]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 16433918HCID 16433918, compound

Product 1

HCID 66778012HCID 66778012, compoundYield 71.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

To a solution (150 mL) of methyl 5-fluoro-3-methyl-1-benzofuran-2-carboxylate (15.4 g) synthesized above in acetonitrile were added N-bromosuccinimide (19.8 g) and 2,2′-azobis(isobutyronitrile) (1.21 g), and the mixture was stirred under argon atmosphere at 50° C. for 2.5 days. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (20-30% ethyl acetate/hexane) to give a white solid. The obtained solid was washed with hexane to give the title object compound (15.1 g, 71%) as a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (20-30% ethyl acetate/hexane)
  3. customto give a white solid
  4. washThe obtained solid was washed with hexane

Sources & evidence

ORD record
ord-7dd68d411ba64cd4a507be06ffe86142
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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