Water → Methyl 5-methanesulfonyl-2-methyl-4-(4-pentafluorosulfanylphenyl-sulfanyl)benzoate

HRID 130625Notes

Reaction equation

[F:1][S:2]([F:13])([F:12])([F:11])([F:10])[C:3]1[CH:8]=[CH:7][C:6]([SH:9])=[CH:5][CH:4]=1.Br[C:15]1[C:24]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:23][C:18]([C:19]([O:21][CH3:22])=[O:20])=[C:17]([CH3:29])[CH:16]=1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[CH3:28][S:25]([C:24]1[C:15]([S:9][C:6]2[CH:7]=[CH:8][C:3]([S:2]([F:10])([F:11])([F:12])([F:13])[F:1])=[CH:4][CH:5]=2)=[CH:16][C:17]([CH3:29])=[C:18]([CH:23]=1)[C:19]([O:21][CH3:22])=[O:20])(=[O:26])=[O:27]

Participants

Conditions

Temperature: 110 °C

Procedure

0.28 g of 4-pentafluorosulfanylthiophenol, 0.36 g of methyl 4-bromo-5-methanesulfonyl-2-methylbenzoate and 0.33 g of K2CO3 were dissolved in 8 ml of anhydrous DMF and stirred at 110° C. for 2 h. The reaction mixture was then poured into 100 ml of water and extracted twice with 100 ml of EA each time. The EA phase was then washed twice with 30 ml of water each time. The residue after drying over MgSO4 and removal of the solvent in vacuo was chromatographed on silica gel with CH2Cl2/DIP 1:2. 320 mg of a colorless foam were obtained.

Workup

extractionextracted twice with 100 ml of EA each time
washThe EA phase was then washed twice with 30 ml of water each time
dry with materialThe residue after drying over MgSO4 and removal of the solvent in vacuo
customwas chromatographed on silica gel with CH2Cl2/DIP 1:2

Sources & evidence

ORD record: ord-e7a78f8d62b145269a17f5d94607ec92
Source dataset: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07381841B2

Reaction notes

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