Dimethyl Sulfoxide → HCID 69412700, compound

HRID 1271123Notes

Reaction equation

HRID 1271123 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1F)[C:5]([OH:7])=[O:6].CC(S)C.C(=O)([O-])[O-:17].[Cs+].[Cs+].Cl[C:23]1C=C(C=[CH:31][CH:32]=1)C(OO)=O.C[S:34](C)=[O:35]>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[S:34]([CH:32]([CH3:31])[CH3:23])(=[O:35])=[O:17])[C:5]([OH:7])=[O:6]

Participants

7

Reactant 5

HCID 679Dimethyl SulfoxideHCID 63642-PropanethiolHCID 10796Cesium carbonateHCID 70297m-Chloroperbenzoic acidHCID 991663,4-Difluorobenzoic acid

Product 1

HCID 69412700HCID 69412700, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A capped scintillation vial containing a mixture of 158 mg (1.0 mmol) of 3,4-difluorobenzoic acid, 186 μL (2.0 mmol) of 2-propanethiol and 652 mg (2.0 mmol) of cesium carbonate in 2.5 mL of DMSO was heated at 50 C for 2.5 days. The reaction mixture was cooled to room temperature and partitioned between ethyl ether and 1M HCl. The organic phase was separated and washed with water and brine. The organic layer was dried (MgSO4) and concentrated in vacuo. The concentrated material was dissolved in 6 mL of THF and treated with a solution of 0.52 g (2.0 mmol) of 3-chloroperoxybenzoic acid (66% by weight) in 4 mL of DCM. The reaction mixture was stirred at rt overnight and then concentrated in vacuo. The residue was dissolved in 5% methanol/CHCl3 and absorbed onto SiO2. Chromatography on SiO2 (5% to 7% methanol/CHCl3) afforded 204 mg (83% yield) of 3-fluoro-4-(propane-2-sulfonyl)-benzoic acid as a white solid.

Workup

  1. additionA capped scintillation vial containing
  2. temperaturewas heated at 50 C for 2.5 days
  3. custompartitioned between ethyl ether and 1M HCl
  4. customThe organic phase was separated
  5. washwashed with water and brine
  6. dry with materialThe organic layer was dried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. dissolutionThe concentrated material was dissolved in 6 mL of THF
  9. concentrationconcentrated in vacuo
  10. dissolutionThe residue was dissolved in 5% methanol/CHCl3
  11. customabsorbed onto SiO2

Sources & evidence

ORD record
ord-d8328ce4650c4d3d8ff2521c575912db
Source dataset
uspto-grants-2007_04
Patent number
US07205307B2

Reaction notes

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