Hydrochloric Acid → Sodium 4-fluorobenzene sulfinate

HRID 2086163Notes

Reaction equation

HRID 2086163 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 grams 257 mmol), sodium sulfite (48.6 grams, 386 mmol), and sodium bicarbonate (108 grams, 1.28 mol) in water was heated to 100° C. The resulting solution was stirred for 1.5 hours at 100° C. then cooled to room temperature, acidified by careful addition of concentrated hydrochloric acid and extracted with ethyl acetate (3 times 250 ml). The combined organic extracts were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated to give the title compound of Step A as a solid (35.8 g). 1H NMR (400 MHz, CDCl3) δ9.78 (s, 1H), 7.77-7.67 (m, 2H), 7.21-7.15 (m, 2H). MS (APCI−) Calc.: 160.0, Found: 195.1 (M+35, Cl− adduct).

Workup

  1. temperaturethen cooled to room temperature
  2. extractionextracted with ethyl acetate (3 times 250 ml)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-8b133f039e6a473b93ef27676357fc3d
Source dataset
uspto-grants-2004_04
Patent number
US06723744B2

Reaction notes

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