Sodium Hydroxide → 5-Carboxy-2-fluorobenzenesulfinic acid

HRID 1825808Notes

Reaction equation

HRID 1825808 reaction equation
S([O-])([O-])=O.[Na+].[Na+].Cl[S:8]([C:11]1[CH:12]=[C:13]([CH:17]=[CH:18][C:19]=1[F:20])[C:14]([OH:16])=[O:15])(=[O:10])=[O:9].[OH-].[Na+]>O>[F:20][C:19]1[CH:18]=[CH:17][C:13]([C:14]([OH:16])=[O:15])=[CH:12][C:11]=1[S:8]([OH:10])=[O:9]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24437Sodium SulfiteHCID 39298913-(Chlorosulfonyl)-4-fluorobenzoic acid

Product 1

HCID 106796785-Carboxy-2-fluorobenzenesulfinic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium sulphite (130 g, 1.034 mol) was added slowly to a solution of 3-chlorosulfonyl-4-fluoro-benzoic acid (49.39 g, 0.207 mol) in water (150 ml) at 0° C. with a vigorous stirring. After the addition was completed the reaction was warmed back to room temperature for 1 hour and the pH of the solution was kept around pH 6–7 with 2N sodium hydroxide solution. The white milky suspension was filtered and the solid washed with 2N sodium hydroxide solution (150 ml) and then water (100 ml). The filtrate was then cooled in an ice bath and concentrated HCl was added until no more precipitate was formed (pH<1). The white precipitate was then filtered, pressed dry and left in a dessicator overnight under vacuum and over activated silica (27.92 g, 66%). m/z (LC-MS, ESP), RT=0.98 min, (M−−1)=203

Workup

  1. additionAfter the addition
  2. filtrationThe white milky suspension was filtered
  3. washthe solid washed with 2N sodium hydroxide solution (150 ml)
  4. temperatureThe filtrate was then cooled in an ice bath
  5. additionconcentrated HCl was added until no more precipitate
  6. customwas formed (pH<1)
  7. filtrationThe white precipitate was then filtered
  8. custompressed dry

Sources & evidence

ORD record
ord-e1550b95f93547b6a0f66a82be8c2832
Source dataset
uspto-grants-2006_05
Patent number
US07049313B2

Reaction notes

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