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Bromoacetic Acid → 1-Chloro-4,5-difluoro-2-(methylsulfonyl)benzene

HRID 20552
Notes
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Reaction equation

HRID 20552 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=1[S:10](Cl)(=[O:12])=[O:11].S([O-])([O-])=O.[Na+].[Na+].[C:20](=O)(O)[O-].[Na+].BrCC(O)=O>O>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=1[S:10]([CH3:20])(=[O:12])=[O:11]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6227Bromoacetic AcidHCID 24437Sodium SulfiteHCID 516892Sodium BicarbonateHCID 27735232-Chloro-4,5-difluorobenzenesulfonyl chloride

Product 1

HCID 593468611-Chloro-4,5-difluoro-2-(methylsulfonyl)benzeneYield 48%

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent
2×

Conditions

Temperature
150 °C

Procedure

2-Chloro-4,5-difluorobenzenesulfonyl chloride (300 mg) was added to a solution of sodium sulfite (306 mg) and sodium bicarbonate (153 mg) in water (4 mL). The mixture was heated to 150° C. in a sealed microwave vial for 400 seconds and allowed to cool. The mixture was treated with bromoacetic acid (253 mg) in water (1 mL), and heated to 150° C. for 300 seconds then allowed to cool, following which the precipitate was removed by filtration and dried in vacuo to give the desired compound (132 mg). The material was used without further purification.

Workup

  1. temperatureto cool
  2. temperatureheated to 150° C. for 300 seconds
  3. temperatureto cool
  4. customwas removed by filtration
  5. customdried in vacuo

Sources & evidence

ORD record
ord-b692961d75f642889f4ac786d8c9eff8
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07745475B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes