Chloroacetic Acid → 3-Bromo-4-fluoro-5-methanesulfonylbenzoic acid

HRID 732510Notes

Reaction equation

HRID 732510 reaction equation
S([O-])([O-])=S.[Na+].[Na+].[C:7](=O)(O)[O-].[Na+].[Br:12][C:13]1[CH:14]=[C:15]([CH:19]=[C:20]([S:23](Cl)(=[O:25])=[O:24])[C:21]=1[F:22])[C:16]([OH:18])=[O:17].ClCC(O)=O.[OH-].[Na+]>O>[Br:12][C:13]1[CH:14]=[C:15]([CH:19]=[C:20]([S:23]([CH3:7])(=[O:25])=[O:24])[C:21]=1[F:22])[C:16]([OH:18])=[O:17]

Participants

7

Reactant 5

HCID 300Chloroacetic AcidHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 15847209sodium thiosulfite anhydrousHCID 509984803-Bromo-4-fluoro-5-(chlorosulfonyl)benzoic acid

Product 1

HCID 688147113-Bromo-4-fluoro-5-methanesulfonylbenzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To sodium thiosulfite (2.6 g, 20.7 mmol) and sodium bicarbonate (1.74 g, 20.7 mmol) in water (20 mL) at 75° C. add 3-bromo-5-chlorosulfonyl-4-fluorobenzoic acid (6.25 g, 19.7 mmol) in portions over 5 min. After 1 h, cool to room temperature and add chloroacetic acid (5.29 g, 56 mmol) and NaOH (1.18 g, 29.5 mmol) and reflux 16 h. Cool to room temperature and collect the title compound as a solid

Workup

  1. temperaturereflux 16 h
  2. temperatureCool to room temperature
  3. customcollect the title compound as a solid

Sources & evidence

ORD record
ord-47919f6767db4f28a9986e82414d5468
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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