Benzoyl Peroxide → Methyl 3-bromomethyl-2-chloro-4-methylsulfonylbenzoate

HRID 842549Notes

Reaction equation

HRID 842549 reaction equation
[Cl:1][C:2]1[C:11]([CH3:12])=[C:10]([S:13]([CH3:16])(=[O:15])=[O:14])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[Br:17]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:17][CH2:12][C:11]1[C:2]([Cl:1])=[C:3]([CH:8]=[CH:9][C:10]=1[S:13]([CH3:16])(=[O:15])=[O:14])[C:4]([O:6][CH3:7])=[O:5]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 15132838Methyl 2-chloro-3-methyl-4-methylsulfonylbenzoate

Product 1

HCID 10969914Methyl 3-bromomethyl-2-chloro-4-methylsulfonylbenzoate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

44.14 g (0.17 mol) of methyl 2-chloro-3-methyl-4-methylsulfonylbenzoate were dissolved in 600 ml of carbon tetrachloride and treated with 29.91 g (0.17 mol) of N-bromosuccinimide and 0.41 g of dibenzoyl peroxide. The mixture was then refluxed and illuminated with a 300 W lamp. The reaction mixture was filtered, the filtrate was concentrated and the residue was taken up in diethyl ether. The solution was treated with n-heptane, and the precipitated solid was filtered off with suction and dried.

Workup

  1. temperatureThe mixture was then refluxed
  2. customilluminated with a 300 W lamp
  3. filtrationThe reaction mixture was filtered
  4. concentrationthe filtrate was concentrated
  5. additionThe solution was treated with n-heptane
  6. filtrationthe precipitated solid was filtered off with suction
  7. customdried

Sources & evidence

ORD record
ord-1bb8c2edefb1447b864599e34a6d1749
Source dataset
uspto-grants-2002_04
Patent number
US06376429B1

Reaction notes

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