N-bromobutanimide → Methyl 3-bromomethyl-4-methanesulfonyl-2-methylbenzoate

HRID 1585461Notes

Reaction equation

HRID 1585461 reaction equation
[CH3:1][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(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:17][CH2:12][C:11]1[C:2]([CH3:1])=[C:3]([CH:8]=[CH:9][C:10]=1[S:13]([CH3:16])(=[O:14])=[O:15])[C:4]([O:6][CH3:7])=[O:5]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 22129435Methyl 2,3-dimethyl-4-methylsulfonylbenzoate

Product 1

HCID 22129433Methyl 3-bromomethyl-4-methanesulfonyl-2-methylbenzoateYield 43.4%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

10.8 g (0.045 mol) of methyl 2,3-dimethyl-4-methanesulfonylbenzoate was dissolved in 80 ml of carbon tetrachloride, and 8.3 g (0.047 mol) of N-bromosuccinimide and 0.1 g of benzoyl peroxide were then added, followed by stirring for 3 hours under heating reflux. After the solution was allowed to cool, insoluble substance was removed by filtration, and the resulting filtrate was washed with an aqueous sodium hydrogen bisulfite solution, and then dried over anhydrous magnesium sulfate. Next, the solvent was distilled off under reduced pressure, the residue was purified through silica gel column chromatography to obtain 6.2 g of methyl 3-bromomethyl-4-methanesulfonyl-2-methylbenzoate in a state of crystals. Yield=43.4%.

Workup

  1. temperatureunder heating
  2. temperaturereflux
  3. temperatureto cool
  4. custominsoluble substance was removed by filtration
  5. washthe resulting filtrate was washed with an aqueous sodium hydrogen bisulfite solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationNext, the solvent was distilled off under reduced pressure
  8. customthe residue was purified through silica gel column chromatography

Sources & evidence

ORD record
ord-c5dec48336e24e0aa3a7b8c2f1b3f5a2
Source dataset
uspto-grants-1999_08
Patent number
US05939360

Reaction notes

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