N-bromobutanimide → HCID 54002298, compound

HRID 262202Notes

Reaction equation

HRID 262202 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.[Br:17]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]=[CH:9][C:10]2[CH:11]=[CH:12][C:13]([CH2:16][Br:17])=[CH:14][CH:15]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 543167421-Chloro-4-[2-(4-methylphenyl)ethenyl]benzene

Product 1

HCID 54002298HCID 54002298, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 5.7 g. (0.025 m) of 4-chloro-4'-methylstilbene (m.p. 196°-197° C.) and 4.43 g. (0.025 m) of N-bromosuccinimide in 124 ml. of carbon tetrachloride was heated at reflux for eight hours. The reaction mixture was filtered hot, allowed to cool and stand overnight and again filtered to remove a small amount of amorphous material. The solvent was removed in vacuo and the residue crystallized from cyclohexane to give 4-(4-chlorostyryl)benzyl bromide, m.p. 130°-132° C. in 85% yield.

Workup

  1. additionA mixture of 5.7 g
  2. temperatureat reflux for eight hours
  3. filtrationThe reaction mixture was filtered hot
  4. temperatureto cool
  5. filtrationagain filtered
  6. customto remove a small amount of amorphous material
  7. customThe solvent was removed in vacuo
  8. customthe residue crystallized from cyclohexane

Sources & evidence

ORD record
ord-256ccd74424e4fa78f4d47e758fbb9ef
Source dataset
uspto-grants-1979_05
Patent number
US04153719

Reaction notes

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