Water → Methyl 5-methanesulfonyl-2-methyl-4-(3-pentafluorosulfanylphenoxy)benzoate

HRID 2358480Notes

Reaction equation

HRID 2358480 reaction equation
[F:1][S:2]([F:13])([F:12])([F:11])([F:10])[C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=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.[Cs+].[Cs+].O>CN(C=O)C>[CH3:28][S:25]([C:24]1[C:15]([O:9][C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([S:2]([F:10])([F:11])([F:12])([F:13])[F:1])[CH:4]=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

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 27792013-(Pentafluorothio)phenolHCID 10590825Methyl 4-bromo-5-methanesulfonyl-2-methylbenzoate

Product 1

HCID 11704977Methyl 5-methanesulfonyl-2-methyl-4-(3-pentafluorosulfanylphenoxy)benzoateYield 80.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5.00 g of 3-pentafluorosulfanylphenol, 6.98 g of methyl 4-bromo-5-methanesulfonyl-2-methylbenzoate (Journal of Medicinal Chemistry (1997), 40(13), 2017) and 22.20 g of Cs2CO3 were stirred in 200 ml of anhydrous DMF at 100° C. for 2 h. The mixture was allowed to cool, and the reaction mixture was poured onto 1 of water and stirred at RT for 16 h. The product was then filtered off and dried under reduced pressure. 8.20 g of pale yellow crystals were obtained, mp 139° C. (with decomposition).

Workup

  1. temperatureto cool
  2. filtrationThe product was then filtered off
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-c0d144a7b2a74e7e91097bcc4053eafe
Source dataset
uspto-grants-2010_07
Patent number
US07763661B2

Reaction notes

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