Methyl 5-methanesulfonyl-4-(4-nitro-3-pentafluorosulfanylphenoxy)-2-methylbenzoate → Methyl 4-(4-amino-3-pentafluorosulfanylphenoxy)-5-methanesulfonyl-2-methylbenzoate

HRID 2358482Notes

Reaction equation

HRID 2358482 reaction equation
[CH3:1][S:2]([C:5]1[C:6]([O:16][C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-])=O)=[C:19]([S:26]([F:31])([F:30])([F:29])([F:28])[F:27])[CH:18]=2)=[CH:7][C:8]([CH3:15])=[C:9]([CH:14]=1)[C:10]([O:12][CH3:13])=[O:11])(=[O:4])=[O:3].[H][H]>CC(O)=O.CO.[Pd]>[NH2:23][C:20]1[CH:21]=[CH:22][C:17]([O:16][C:6]2[C:5]([S:2]([CH3:1])(=[O:3])=[O:4])=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[C:8]([CH3:15])[CH:7]=2)=[CH:18][C:19]=1[S:26]([F:30])([F:31])([F:27])([F:28])[F:29]

Participants

6

Reactant 2

HCID 11648857Methyl 5-methanesulfonyl-4-(4-nitro-3-pentafluorosulfanylphenoxy)-2-methylbenzoateHCID 178418361HCID 178418361, compound2×

Product 1

HCID 59832568Methyl 4-(4-amino-3-pentafluorosulfanylphenoxy)-5-methanesulfonyl-2-methylbenzoateYield 95.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalyst2×HCID 176Acetic AcidSolvent2×HCID 887MethanolSolvent2×

Procedure

3.80 g of methyl 5-methanesulfonyl-4-(4-nitro-3-pentafluorosulfanyl-phenoxy)-2-methylbenzoate (example 1) were dissolved in 30 ml of HOAc and 30 ml of MeOH, admixed with 200 mg of Pd/C (10%) and hydrogenated under 6 bar of hydrogen pressure for 24 h. Since the reaction was not yet complete, a further 300 mg of Pd/C (10%), 30 ml of HOAc and 30 ml of MeOH were added and the mixture was hydrogenated under 6 bar of hydrogen pressure for a further 24 h. Subsequently, the catalyst was filtered off and the solvents were removed under reduced pressure. 3.4 g of a light gray solid were obtained, mp 175° C. (with decomposition).

Workup

  1. filtrationSubsequently, the catalyst was filtered off
  2. customthe solvents were removed under reduced pressure

Sources & evidence

ORD record
ord-5c7d0b2f9e8b404a9b281243e74a14e3
Source dataset
uspto-grants-2010_07
Patent number
US07763661B2

Reaction notes

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