Dimethyl Sulfoxide → HCID 12852222, compound

HRID 1065526Notes

Reaction equation

HRID 1065526 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]1[CH:8]=[CH:7][C:6]([O:9][C:10]2[CH:21]=[CH:20][C:13]([O:14][CH:15]([CH3:19])[C:16]([OH:18])=[O:17])=[CH:12][CH:11]=2)=[CH:5][CH:4]=1.C(=O)(O)[O-].[Na+].C(Br)(C)(C)C.[CH3:34][S:35]([CH3:37])=O>C(OCC)(=O)C>[CH3:34][S:35][CH2:37][O:17][C:16](=[O:18])[CH:15]([O:14][C:13]1[CH:12]=[CH:11][C:10]([O:9][C:6]2[CH:5]=[CH:4][C:3]([C:2]([F:22])([F:23])[F:1])=[CH:8][CH:7]=2)=[CH:21][CH:20]=1)[CH3:19]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 10485t-Butyl bromideHCID 181206TrifopHCID 516892Sodium Bicarbonate

Product 1

HCID 12852222HCID 12852222, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

100 g (0.03 mol) of 2-[p-[(α,α,α-trifluoro-p-tolyl)oxy]phenoxy]-propionic acid and 252 g (3.0 mol) of sodium bicarbonate are suspended in 2.5 liters of dimethyl sulphoxide and thereafter treated slowly with 336.5 ml (3.0 mol) of tert.butyl bromide. The mixture is stirred at room temperature overnight. The mixture, including the separated thick precipitate, is subsequently taken up in 5 liters of ethyl acetate. The ethyl acetate solution is washed twice with 1 liter of water, dried over sodium sulphate and evaporated. The residue is chromatographed on a 10-fold amount of silica gel with hexane/ethyl acetate (7:1) and the eluate is evaporated. There is obtained 2-[p-[(α,α,α-trifluoro-p-tolyl)oxy]phenoxy]-propionic acid [(methylthio)methyl]ester in the form of an oil.

Workup

  1. washThe ethyl acetate solution is washed twice with 1 liter of water
  2. dry with materialdried over sodium sulphate
  3. customevaporated
  4. customThe residue is chromatographed on a 10-fold amount of silica gel with hexane/ethyl acetate (7:1)
  5. customthe eluate is evaporated

Sources & evidence

ORD record
ord-d8a0452934fe412f9dff6383791f9f12
Source dataset
uspto-grants-1982_05
Patent number
US04329488

Reaction notes

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