Benzoyl Peroxide → (Z)-2-bromomethyl cinnamic acid

HRID 1456920Notes

Reaction equation

HRID 1456920 reaction equation
[CH3:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[CH:4]=[CH:5][C:6]([OH:8])=[O:7].[Br:13]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:13][CH2:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1/[CH:4]=[CH:5]\[C:6]([OH:8])=[O:7]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 983063-(2-Methylphenyl)prop-2-enoic acid

Product 1

HCID 86750270(Z)-2-bromomethyl cinnamic acid

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 2 g (12.34 mmol) of (E) 2-methyl cinnamic acid, 2.19 g (12.34 mmol) of N-bromosuccinimide (NBS) and a catalytic amount of benzoyl peroxide in 6 ml of CCl4 are heated under reflux for 6 hours. The residue is filtered and washed with ether. The organic phase is successively washed with a 1N HCl aqueous solution then with water. It is dried on MgSO4, filtered and evaporated to dryness.

Workup

  1. temperatureunder reflux for 6 hours
  2. filtrationThe residue is filtered
  3. washwashed with ether
  4. washThe organic phase is successively washed with a 1N HCl aqueous solution
  5. customIt is dried on MgSO4
  6. filtrationfiltered
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-9abd99b8ace14274ba7227aa306ba80a
Source dataset
uspto-grants-1998_12
Patent number
US05846956

Reaction notes

Loading…