N-bromobutanimide → Ethyl 1-methyl-1-(4-bromomethylphenyl)ethanesulfonate

HRID 1005395Notes

Reaction equation

HRID 1005395 reaction equation
[CH3:1][C:2]([C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=1)([S:4]([O:7][CH2:8][CH3:9])(=[O:6])=[O:5])[CH3:3].[Br:17]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(Cl)(=O)C1C=CC=CC=1>[CH3:1][C:2]([C:10]1[CH:15]=[CH:14][C:13]([CH2:16][Br:17])=[CH:12][CH:11]=1)([S:4]([O:7][CH2:8][CH3:9])(=[O:5])=[O:6])[CH3:3]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 21706484Ethyl 1-methyl-1-(4-methylphenyl)ethanesulfonate

Product 1

HCID 21706518Ethyl 1-methyl-1-(4-bromomethylphenyl)ethanesulfonateYield 105.4%

Reagents, catalysts & solvents 2

HCID 7412Benzoyl chlorideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of ethyl 1-methyl-1-(4-methylphenyl)ethanesulfonate (0.458 g, 1.89 mmol) in carbon tetrachloride (8 mL) was added N-bromosuccinimide (0.370 g, 2.08 mmol) and benzoyl chloride (0.009 g). The mixture was heated under reflux for 1.5 hours, cooled to rt, and filtered. The filtrate was washed with aqueous sodium bicarbonate and brine, dried, filtered and evaporated to give crude ethyl 1-methyl-1-(4-bromomethylphenyl)ethanesulfonate (0.64 g, 100%) which was used directly in the next reaction.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 1.5 hours
  3. filtrationfiltered
  4. washThe filtrate was washed with aqueous sodium bicarbonate and brine
  5. customdried
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-e2447f1540014d6c84d0a72d1913ca49
Source dataset
uspto-grants-2000_04
Patent number
US06054470

Reaction notes

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