2-Bromobutanoic acid → 1-(Methylsulfonyl)-3-(trifluoromethyl)benzene

HRID 1957951Notes

Reaction equation

HRID 1957951 reaction equation
S([O-])([O-])=O.[Na+].[Na+].C(=O)(O)[O-].[Na+].[F:12][C:13]([F:25])([F:24])[C:14]1[CH:15]=[C:16]([S:20](Cl)(=[O:22])=[O:21])[CH:17]=[CH:18][CH:19]=1.[OH-].[Na+].[CH2:28](C(Br)C(O)=O)C>O>[CH3:28][S:20]([C:16]1[CH:17]=[CH:18][CH:19]=[C:14]([C:13]([F:25])([F:24])[F:12])[CH:15]=1)(=[O:22])=[O:21]

Participants

7

Reactant 5

HCID 66552-Bromobutanoic acidHCID 14798Sodium HydroxideHCID 24437Sodium SulfiteHCID 516892Sodium BicarbonateHCID 27332503-(Trifluoromethyl)benzenesulfonyl chloride

Product 1

HCID 27607611-(Methylsulfonyl)-3-(trifluoromethyl)benzeneYield 22.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A suspension of sodium sulfite (3.0 g, 24 mmol), sodium bicarbonate (3.7 g; 44 mmol and 3-trifluormethylbenzenesulfonylchloride (5.0 g; 20 mmol) in 70 mL water, was heated at 75° C. for 1 hour. Then 5 mL 50% aqueous sodium hydroxide to solution and ethyl bromoacetic acid (2.65 mL; 22 mmol) was added and the mixture was refluxed for 30 hours. Then the mixture was extracted with dichloromethane and concentrated to provide 1 g (4.46 mmol; 20% yield) of 1-methanesulfonyl-3-trifluoromethylbenzene as a solid.

Workup

  1. temperaturethe mixture was refluxed for 30 hours
  2. extractionThen the mixture was extracted with dichloromethane
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-a4daa85c5c7943ca89d9a4aef2eec4b0
Source dataset
uspto-grants-2013_04
Patent number
US08410100B2

Reaction notes

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