m-Chloroperbenzoic acid → 2,2-dimethyl-5-{3-fluoro-4-(methylsulfinyl)phenyl}-4-(3-fluorophenyl)-3(2H)-furanone

HRID 2298326Notes

Reaction equation

HRID 2298326 reaction equation
[CH3:1][C:2]1([CH3:24])[C:6](=[O:7])[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[CH:9]=2)=[C:4]([C:15]2[CH:20]=[CH:19][C:18]([S:21][CH3:22])=[C:17]([F:23])[CH:16]=2)[O:3]1.ClC1C=C(C=CC=1)C(OO)=[O:30].C(=O)(O)[O-].[Na+]>ClCCl>[CH3:1][C:2]1([CH3:24])[C:6](=[O:7])[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[CH:9]=2)=[C:4]([C:15]2[CH:20]=[CH:19][C:18]([S:21]([CH3:22])=[O:30])=[C:17]([F:23])[CH:16]=2)[O:3]1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 18385856HCID 18385856, compound

Product 1

HCID 183857282,2-dimethyl-5-{3-fluoro-4-(methylsulfinyl)phenyl}-4-(3-fluorophenyl)-3(2H)-furanoneYield 95.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (2,2-dimethyl)-5-{3-fluoro-4-(methylthio)phenyl}-4-(3-fluorophenyl)-3(2H)-furanone (1.6 g) in 50 ml dichloromethane, which was prepared by a procedure similar to the procedure employed for Example 264, 1.25 g of m-chloroperoxybenzoic acid at 0° C. The reaction solution was stirred for one and half hours at the temperature, after which 30 ml 5% aqueous sodium bicarbonate was added and the solution was stirred for another 10 minutes. Then the reaction mixture was concentrated in vacuo, and the resulting residue was extracted with 50 ml water and dichloromethane (30 ml×3). The organic layer was concentrated in vacuo and was purified by column chromatography (hexane/ethylacetate=1:1) to give 1.6 g of 2,2-dimethyl-5-{3-fluoro-4-(methylsulfinyl)phenyl}-4-(3-fluorophenyl)-3(2H)-furanone as a solid. mp: 148-149° C. NMR: δ1.58 (s, 6H), 2.87 (s, 3H), 7.06 (m, 3H), 7.36(m, 1H), 7.42 (dd, J=10.5, 1.8 Hz, 1H), 7.66 (dd, J=8.4, 1.8 Hz, 1H), 7.87 (dd, J=8.1. 6.9 Hz, 1H). IR (cm−1): 1700, 1623, 1420, 1261, 1216, 1192, 1135, 1077.

Workup

  1. stirringthe solution was stirred for another 10 minutes
  2. concentrationThen the reaction mixture was concentrated in vacuo
  3. extractionthe resulting residue was extracted with 50 ml water and dichloromethane (30 ml×3)
  4. concentrationThe organic layer was concentrated in vacuo
  5. customwas purified by column chromatography (hexane/ethylacetate=1:1)

Sources & evidence

ORD record
ord-f5e844a2f45b4d69ac0d13b205ef1abf
Source dataset
uspto-grants-2002_12
Patent number
US06492416B1

Reaction notes

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