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

HRID 1857309Notes

Reaction equation

HRID 1857309 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].C1C(=O)N([Br:24])C(=O)C1>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:24][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 143.8%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

29.69 g of methyl 2,3-dimethyl-4-methylsulfonylbenzoate was dissolved in 260 ml of carbon tetrachloride, and 22.93 g of NBS and 1.0 g of benzoyl peroxide were added to heat at reflux for 2.5 hours. The reaction solution was cooled down, and insoluble matter was separated by filtration. The filtrate was concentrated under reduced pressure to give 56.58 g of viscous oil. The obtained oil was purified by column chromatography on silica gel with n-hexane/ethyl acetate=5/1 to give 18.98 g of the title compound as white crystals.

Workup

  1. temperatureto heat
  2. temperatureat reflux for 2.5 hours
  3. temperatureThe reaction solution was cooled down
  4. custominsoluble matter was separated by filtration
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-4f4f2f71648b43c89d184cd8868194a9
Source dataset
uspto-grants-2000_11
Patent number
US06147031

Reaction notes

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