Bromine → HCID 20386067, compound

HRID 46985Notes

Reaction equation

HRID 46985 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-6a8b1955e7b246738545bc6c90809a31
Source dataset
uspto-grants-1979_11
Patent number
US04175203

Reaction notes

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