Hydrochloric Acid → 4-Bromo-1-(methanesulfonyl)-2-methylbenzene

HRID 1496850Notes

Reaction equation

HRID 1496850 reaction equation
S([O-])([O-])=O.[Na+].[Na+].C([O-])(O)=O.[Na+].[Br:12][C:13]1[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[C:15]([CH3:23])[CH:14]=1.Br[CH2:25]C(O)=O.Cl>O>[Br:12][C:13]1[CH:18]=[CH:17][C:16]([S:19]([CH3:25])(=[O:21])=[O:20])=[C:15]([CH3:23])[CH:14]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6227Bromoacetic AcidHCID 24437Sodium SulfiteHCID 516892Sodium BicarbonateHCID 27813384-Bromo-2-methylbenzenesulfonyl chloride

Product 1

HCID 206167654-Bromo-1-(methanesulfonyl)-2-methylbenzeneYield 44.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
75 °C

Procedure

235 mg Sodium sulfite and 470 mg NaHCO3 were dissolved in 1.75 mL of water and heated to 75° C. 500 mg of 4-Bromo-2-methyl-benzenesulfonyl chloride were added in portions within 10 min (gas formation) and the mixture stirred for 1 h at 75° C. 387 mg of Bromoacetic acid and 150 μL of water was added in small portions and the mixture stirred at 105° C. overnight. After cooling to 25° C. the mixture was acidified to pH 1 using 4N HCl. The resulting precipitate was collected and washed with water to yield 205 mg solid.

Workup

  1. stirringthe mixture stirred at 105° C. overnight
  2. temperatureAfter cooling to 25° C. the mixture
  3. customThe resulting precipitate was collected
  4. washwashed with water

Sources & evidence

ORD record
ord-3e57dc85702c4f478f743857d35ce299
Source dataset
uspto-grants-2015_12
Patent number
US09199937B2

Reaction notes

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