Bromine → HCID 20386067, compound

HRID 26618Notes

Reaction equation

HRID 26618 reaction equation
[C:1]([CH2:3][C:4]1[CH:14]=[CH:13][C:7]([CH2:8][CH2:9]C(O)=O)=[CH:6][CH:5]=1)#[N:2].[Br:15]Br>C(Cl)(Cl)(Cl)Cl>[Br:15][CH2:9][CH2:8][C:7]1[CH:13]=[CH:14][C:4]([CH2:3][C:1]#[N:2])=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 20386113p-Cyanomethylhydrocinnamic acid

Product 1

HCID 20386067HCID 20386067, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of p-cyanomethylhydrocinnamic acid (18.9 g., 0.1 mole), red mercuric oxide (17.2 g., 0.08 mole), and carbon tetrachloride (180 ml.) is stirred at room temperature while bromine (16.0 g., 0.1 mole) is added dropwise during 40 minutes. The resulting mixture is heated at reflux for 1 hour. The mixture is then cooled, filtered, washed with dilute hydrochloric acid and water, and dried over magnesium sulfate. The solution is evaporated to leave the product as a yellow residual oil. It is purified by column chromatography on silica gel with benzene elution.

Workup

  1. additionis added dropwise during 40 minutes
  2. temperatureThe resulting mixture is heated
  3. temperatureat reflux for 1 hour
  4. temperatureThe mixture is then cooled
  5. filtrationfiltered
  6. washwashed with dilute hydrochloric acid and water
  7. dry with materialdried over magnesium sulfate
  8. customThe solution is evaporated

Sources & evidence

ORD record
ord-ace078609a414e19a76a0649735888b0
Source dataset
uspto-grants-1979_04
Patent number
US04150235

Reaction notes

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