Benzoyl Peroxide → HCID 18694859, compound

HRID 1871061Notes

Reaction equation

HRID 1871061 reaction equation
[Cl:1][C:2]1[C:11]([CH3:12])=[C:10]([O:13][CH3:14])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[Br:15]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:15][CH2:12][C:11]1[C:2]([Cl:1])=[C:3]([CH:8]=[CH:9][C:10]=1[O:13][CH3:14])[C:4]([O:6][CH3:7])=[O:5]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 18694844HCID 18694844, compound

Product 1

HCID 18694859HCID 18694859, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To 50 ml carbon tetrachloride, was dissolved methyl 2-chloro-4-methoxy-3-methylbenzoate in an amount of 5.0 g (0.025 mole), and the resulting solution was then stirred for 4 hours under reflux and heating after the addition of N-bromosuccinimide in an amount of 4.9 g (0.028 mole) and benzoyl peroxide in an amount of 0.1 g into the solution. After cooling the mixture, insoluble material therein were separated by filtration, and the filtrate was washed with aqueous solution of sodium hydrogenbisulfite and then dried with anhydrous magnesium sulfate. The solvent remained in the filtrate was condensed under reduced pressure to obtain methyl 3-bromomethyl-2-chloro-4-methoxybenzoate in an amount of 7.5 g in crude crystalline form.

Workup

  1. temperatureunder reflux
  2. temperatureheating
  3. temperatureAfter cooling the mixture, insoluble material
  4. customtherein were separated by filtration
  5. washthe filtrate was washed with aqueous solution of sodium hydrogenbisulfite
  6. dry with materialdried with anhydrous magnesium sulfate
  7. customcondensed under reduced pressure

Sources & evidence

ORD record
ord-c7e39c98f38e4a5ebb81cfad6b1f4e4a
Source dataset
uspto-grants-2000_08
Patent number
US06100421

Reaction notes

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