Sulfuric Acid → 2-Fluoro-5-sulfinobenzoic acid

HRID 1931002Notes

Reaction equation

HRID 1931002 reaction equation
Cl[S:2]([C:5]1[CH:6]=[CH:7][C:8]([F:14])=[C:9]([CH:13]=1)[C:10]([OH:12])=[O:11])(=[O:4])=[O:3].S([O-])([O-])=O.[Na+].[Na+].[OH-].[Na+].OS(O)(=O)=O>O>[F:14][C:8]1[CH:7]=[CH:6][C:5]([S:2]([OH:4])=[O:3])=[CH:13][C:9]=1[C:10]([OH:12])=[O:11]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 24437Sodium SulfiteHCID 6089842-Fluoro-5-chlorosulfonylbenzoic acid

Product 1

HCID 577535332-Fluoro-5-sulfinobenzoic acidYield 72%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

264 mmol 5-Chlorosulfonyl-2-fluoro-benzoic acid (CAS: 37098-75-2) was added portionwise onto a solution of 1.98 mol sodium sulfite in 1 L of water. The reaction mixture was kept under basic conditions by the addition of the proper amount of 20% NaOH and was stirred at room temperature for 45 minutes. After such time the reaction mixture was cooled down with an ice bath and was then acidified by the addition of 20% H2SO4 solution until reaching pH 2. Water was evaporated and 600 ml methanol was added. The mixture was stirred overnight and filtrated. The filtrate was evaporated and dried to yield the title compound as a white solid (72%). MS (m/e): 203.0 ([M−H, 100%)

Workup

  1. temperatureAfter such time the reaction mixture was cooled down with an ice bath
  2. customWater was evaporated
  3. addition600 ml methanol was added
  4. stirringThe mixture was stirred overnight
  5. filtrationfiltrated
  6. customThe filtrate was evaporated
  7. customdried

Sources & evidence

ORD record
ord-70fe8cdb375343009480609cb3434057
Source dataset
uspto-grants-2012_05
Patent number
US08188139B2

Reaction notes

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