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

HRID 1594658Notes

Reaction equation

HRID 1594658 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-86bafae9a2f2404b8299666ac0eb2f7b
Source dataset
uspto-grants-2001_09
Patent number
US06284768B1

Reaction notes

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