Hydrochloric Acid → Sodium 4-fluorobenzene sulfinate

HRID 584020Notes

Reaction equation

HRID 584020 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.S([O-])([O-])=O.[Na+].[Na+].C(=O)(O)[O-].[Na+].Cl>O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([OH:10])=[O:9])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 95884-Fluorobenzenesulfonyl chlorideHCID 24437Sodium SulfiteHCID 516892Sodium Bicarbonate

Product 1

HCID 421250Sodium 4-fluorobenzene sulfinateYield 87%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-fluorobenzenesulfonyl chloride (50.0 g, 257 mmol), sodium sulfite (48.6 g, 386 mmol), and sodium bicarbonate (108 g, 1.28 mol) in water was heated to 100° C. The resulting solution was stirred for 1.5 h at 100° C., then cooled to RT and acidified by careful addition of concentrated hydrochloric acid. The resulting precipitate was extracted with EtOAc (3×250 mL). The combined extracts were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated. Drying in vacuo gave the title compound of Step A as a solid (35.8 g). MS (APCl−) Calc.: 160.0. Found: 195.1 (M+35, Cl− adduct).

Workup

  1. temperaturecooled to RT
  2. extractionThe resulting precipitate was extracted with EtOAc (3×250 mL)
  3. washThe combined extracts were washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customDrying in vacuo

Sources & evidence

ORD record
ord-fd463797882c42359a9d2ea3072f1c6e
Source dataset
uspto-grants-2005_08
Patent number
US06924310B2

Reaction notes

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