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

HRID 1379108Notes

Reaction equation

HRID 1379108 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 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 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-26c82579313449f0b52c78b8e455938e
Source dataset
uspto-grants-1997_09
Patent number
US05670531

Reaction notes

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