Chloroform → Methyl 3-bromomethyl-2-chloro-4-methylsulfonylbenzoate

HRID 1682144Notes

Reaction equation

HRID 1682144 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]Br.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C(Cl)(Cl)Cl>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

6

Reactant 4

HCID 6212ChloroformHCID 7187Benzoyl PeroxideHCID 24408BromineHCID 15132838Methyl 2-chloro-3-methyl-4-methylsulfonylbenzoate

Product 1

HCID 10969914Methyl 3-bromomethyl-2-chloro-4-methylsulfonylbenzoateYield 83.9%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

12.1 g of methyl 2-chloro-4-methanesulfonyl-3-methylbenzoate was dissolved in 250 ml of carbon tetrachloride, and the solution was refluxed under stirring. Then, 7.5 g of bromine and 1 g of benzoyl peroxide were gradually added thereto over a period of 30 minutes, and the solution was further refluxed for 4 hours under heating. After cooling, 200 ml of chloroform was added thereto, and the mixture was washed with a 5% sodium hydrogensulfite aqueous solution. The organic layer was separated and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain a crude product. The crude product was washed with ethyl ether to obtain 13.2 g of crystals of the desired product. Melting point: 77°-78° C.

Workup

  1. temperaturethe solution was refluxed
  2. temperaturethe solution was further refluxed for 4 hours
  3. temperatureunder heating
  4. temperatureAfter cooling
  5. washthe mixture was washed with a 5% sodium hydrogensulfite aqueous solution
  6. customThe organic layer was separated
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationThe solvent was distilled off under reduced pressure
  9. customto obtain a crude product
  10. washThe crude product was washed with ethyl ether

Sources & evidence

ORD record
ord-9373217ec9744ccc9d03a6589d8bb0ab
Source dataset
uspto-grants-1992_12
Patent number
US05175299

Reaction notes

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