N-bromobutanimide → HCID 18946975, compound

HRID 248405Notes

Reaction equation

HRID 248405 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]3[CH:18]=[CH:17][CH:16]=[CH:15][C:10]=3[O:11][C:12]=2[C:13]#[N:14])=[CH:4][CH:3]=1.[Br:19]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.N(C(C)(C)C#N)=NC(C)(C)C#N>[Br:19][CH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]3[CH:18]=[CH:17][CH:16]=[CH:15][C:10]=3[O:11][C:12]=2[C:13]#[N:14])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 20093029HCID 20093029, compound

Product 1

HCID 18946975HCID 18946975, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 3-(4-methylphenyl)benzo[b]furan-2-carbonitrile (239 mg), N-bromosuccinimide (182 mg), and 2,2'-azobisisobutyronitrile (10 mg) in carbon tetrachloride (5 ml) was refluxed for 5 hours and cooled to ambient temperature. The precipitates were filtered off. The filtrate was washed with aqueous sodium bicarbonate solution (×3), dried, and concentrated in vacuo to give a yellow oil, which was crystallized from n-hexane to yield 3-(4-bromomethylphenyl)benzo[b]furan-2-carbonitrile (300 mg) as a yellow solid.

Workup

  1. temperaturewas refluxed for 5 hours
  2. filtrationThe precipitates were filtered off
  3. washThe filtrate was washed with aqueous sodium bicarbonate solution (×3)
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customto give a yellow oil, which
  7. customwas crystallized from n-hexane

Sources & evidence

ORD record
ord-cf9456a135ab43fcb7cb2fc1eeeb16af
Source dataset
uspto-grants-1993_05
Patent number
US05210092

Reaction notes

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