Hydrochloric Acid → Sodium 4-(2-methanesulfonyl-4-methoxycarbonyl-5-methylphenoxy)-2-pentafluorosulfanylbenzenesulfinate

HRID 2358483Notes

Reaction equation

HRID 2358483 reaction equation
[CH3:1][O:2][C:3](=[O:32])[C:4]1[CH:9]=[C:8]([S:10]([CH3:13])(=[O:12])=[O:11])[C:7]([O:14][C:15]2[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[C:17]([S:25]([F:30])([F:29])([F:28])([F:27])[F:26])[CH:16]=2)=[CH:6][C:5]=1[CH3:31].[O-]S([O-])=O.[Na+:37].[Na+].[OH-].[Na+].Cl>O>[CH3:13][S:10]([C:8]1[CH:9]=[C:4]([C:3]([O:2][CH3:1])=[O:32])[C:5]([CH3:31])=[CH:6][C:7]=1[O:14][C:15]1[CH:20]=[CH:19][C:18]([S:21]([O-:23])=[O:22])=[C:17]([S:25]([F:26])([F:27])([F:28])([F:30])[F:29])[CH:16]=1)(=[O:11])=[O:12].[Na+:37]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24437Sodium SulfiteHCID 59832570Methyl 4-(4-chlorosulfonyl-3-pentafluorosulfanylphenoxy)-5-methanesulfonyl-2-methylbenzoate

Product 1

HCID 86616338Sodium 4-(2-methanesulfonyl-4-methoxycarbonyl-5-methylphenoxy)-2-pentafluorosulfanylbenzenesulfinate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

3.5 g of methyl 4-(4-chlorosulfonyl-3-pentafluorosulfanylphenoxy)-5-methanesulfonyl-2-methylbenzoate (example 3) were added in portions to a solution, at 70° C., of 8.10 g of Na2SO3 in 75 ml of water and kept at about pH=10 with 10 molar aqueous NaOH solution. Subsequently, the mixture was stirred at 70° C. for 45 minutes, then allowed to cool and adjusted to pH=2 with aqueous HCl solution. The mixture was extracted 3 times with 200 ml each time of EA. The mixture was dried over MgSO4 and the solvent was removed under reduced pressure. The residue was suspended in 100 ml of water and adjusted to pH=10 with a 2 molar aqueous NaOH solution, and the volatile constituents were removed under reduced pressure. The mixture was subsequently extracted twice with 100 ml each time of toluene and then coevaporated with 100 ml of anhydrous DMF, and the residue (3.0 g) was reacted further without purification.

Workup

  1. temperatureto cool
  2. extractionThe mixture was extracted 3 times with 200 ml each time of EA
  3. dry with materialThe mixture was dried over MgSO4
  4. customthe solvent was removed under reduced pressure
  5. customthe volatile constituents were removed under reduced pressure
  6. extractionThe mixture was subsequently extracted twice with 100 ml each time of toluene
  7. customthe residue (3.0 g) was reacted further without purification

Sources & evidence

ORD record
ord-26d872e30d3c46379c20250156bb3fb6
Source dataset
uspto-grants-2010_07
Patent number
US07763661B2

Reaction notes

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