Dimethylformamide → Methyl 5-methanesulfonyl-4-(4-methoxysulfinyl-3-pentafluorosulfanylphenoxy)-2-methylbenzoate

HRID 2358484Notes

Reaction equation

HRID 2358484 reaction equation
[CH3:1][S:2]([C:5]1[CH:26]=[C:25]([C:27]([O:29][CH3:30])=[O:28])[C:24]([CH3:31])=[CH:23][C:6]=1[O:7][C:8]1[CH:13]=[CH:12][C:11]([S:14]([O-:16])=[O:15])=[C:10]([S:17]([F:22])([F:21])([F:20])([F:19])[F:18])[CH:9]=1)(=[O:4])=[O:3].[Na+].[CH3:33]N([CH:36]=[O:37])C>>[CH3:1][S:2]([C:5]1[C:6]([O:7][C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH3:33])(=[O:16])=[O:15])=[C:10]([S:17]([F:19])([F:18])([F:20])([F:21])[F:22])[CH:9]=2)=[CH:23][C:24]([CH3:31])=[C:25]([CH:26]=1)[C:27]([O:29][CH3:30])=[O:28])(=[O:3])=[O:4].[CH3:1][S:2]([C:5]1[C:6]([O:7][C:8]2[CH:13]=[CH:12][C:11]([S:14]([O:37][CH3:36])=[O:15])=[C:10]([S:17]([F:20])([F:22])([F:21])([F:18])[F:19])[CH:9]=2)=[CH:23][C:24]([CH3:31])=[C:25]([CH:26]=1)[C:27]([O:29][CH3:30])=[O:28])(=[O:3])=[O:4]

Participants

4

Reactant 2

HCID 6228DimethylformamideHCID 86616338Sodium 4-(2-methanesulfonyl-4-methoxycarbonyl-5-methylphenoxy)-2-pentafluorosulfanylbenzenesulfinate

Product 2

HCID 59832569Methyl 5-methanesulfonyl-4-(4-methoxysulfinyl-3-pentafluorosulfanylphenoxy)-2-methylbenzoateHCID 59832571Methyl 5-methanesulfonyl-4-(4-methanesulfonyl-3-pentafluorosulfanylphenoxy)-2-methylbenzoate

Conditions

Temperature
45 °C

Procedure

3.0 g of sodium 4-(2-methanesulfonyl-4-methoxycarbonyl-5-methyl-phenoxy)-2-pentafluorosulfanylbenzenesulfinate (example 4) were dissolved in 100 ml of anhydrous DMF, 4.0 g of CH31 were added and the mixture was stirred at 45° C. for 9 h. The reaction mixture was subsequently left to stand at RT for 2 days. The solvent was then removed under reduced pressure and the residue taken up with 100 ml of water and 100 ml of EA. 50 ml of a 5% aqueous NaHSO4 solution were then added and the phases were separated. Subsequently, the mixture was extracted 3 times with 100 ml each time of EA. The mixture was dried over MgSO4, the solvent was removed under reduced pressure and the residue was chromatographed on silica gel with 1:1 MTB/DIP. 0.59 g of methyl 5-methanesulfonyl-4-(4-methanesulfonyl-3-pentafluorosulfanylphenoxy)-2-methylbenzoate and 0.49 g of methyl 5-methanesulfonyl-4-(4-methoxysulfinyl-3-pentafluorosulfanylphenoxy)-2-methylbenzoate were obtained.

Workup

  1. addition4.0 g of CH31 were added
  2. waitThe reaction mixture was subsequently left
  3. waitto stand at RT for 2 days
  4. customThe solvent was then removed under reduced pressure
  5. addition50 ml of a 5% aqueous NaHSO4 solution were then added
  6. customthe phases were separated
  7. extractionSubsequently, the mixture was extracted 3 times with 100 ml each time of EA
  8. dry with materialThe mixture was dried over MgSO4
  9. customthe solvent was removed under reduced pressure
  10. customthe residue was chromatographed on silica gel with 1:1 MTB/DIP

Sources & evidence

ORD record
ord-d790bfbe819d4064b299106b1855f317
Source dataset
uspto-grants-2010_07
Patent number
US07763661B2

Reaction notes

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