N-bromobutanimide → HCID 54087782, compound

HRID 867091Notes

Reaction equation

HRID 867091 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)=[CH:9][CH3:10])=[CH:4][CH:3]=1.[Br:17]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)=[CH:9][CH2:10][Br:17])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 54471371HCID 54471371, compound

Product 1

HCID 54087782HCID 54087782, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 7.0 g (0.024 mol) of 1-(4-bromophenyl)-1-(3-pyridyl)-propene and 4.6 g (0.024 mol) of N-bromosuccinimide in 600 ml of carbontetrachloride was heated with stirring to 80° C. Then 0.5 g. of α,α-azabisbutyronitrile was added as radical initiator and the mixture was refluxed for 2 hours. After cooling to ambient temperature, the reaction mixture was filtered and the filtrate was evaporated in vacuo to 100 ml. NMR on the residual solution indicated a 1:1-mixture of the E- and Z-3-(4-bromophenyl)-3-(3-pyridyl)allylbromides. This solution was used directly in the preparation of the end product without further purification.

Workup

  1. temperaturewas heated
  2. additionof α,α-azabisbutyronitrile was added as radical initiator
  3. temperaturethe mixture was refluxed for 2 hours
  4. temperatureAfter cooling to ambient temperature
  5. filtrationthe reaction mixture was filtered
  6. customthe filtrate was evaporated in vacuo to 100 ml
  7. customThis solution was used directly in the preparation of the end product without further purification

Sources & evidence

ORD record
ord-30f324fc0a774d4c92d5202715781a2e
Source dataset
uspto-grants-1978_07
Patent number
US04102887

Reaction notes

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