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

HRID 269418Notes

Reaction equation

HRID 269418 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-pentafluorosulfanylphenoxy)-2-methyl-benzoate were dissolved in 30 ml of HOAc and 30 ml of MeOH, 200 mg of Pd/C (10%) were added, and hydrogenation was carried out under a pressure of 6 bar of hydrogen for 24 h. Since reaction was still incomplete, a further 300 mg of Pd/C (10%), 30 ml of HOAc and 30 ml of MeOH was added, and hydrogenation was continued under a pressure of 6 bar of hydrogen for 24 h. The catalyst was then filtered off and the solvents were removed in vacuo. 3.4 g of a pale gray solid were obtained, mp 175° C. (with decomposition).

Workup

  1. customSince reaction
  2. filtrationThe catalyst was then filtered off
  3. customthe solvents were removed in vacuo

Sources & evidence

ORD record
ord-eb6e6cde35fb41b3a2b3a0c3370f64d0
Source dataset
uspto-grants-2008_11
Patent number
US07446225B2

Reaction notes

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