m-Chloroperbenzoic acid → (4'-Fluoro-3,3',5-trimethyl-[1,1'-biphenyl]-2-yl-methyl)phenyl sulfoxide

HRID 2119246Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2119246
ClC1C=CC=C(C(OO)=[O:9])C=1.[F:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[C:23]([CH3:25])[CH:22]=[C:21]([CH3:26])[C:20]=2[CH2:27][S:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:15][C:14]=1[CH3:35]>>[F:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[C:23]([CH3:25])[CH:22]=[C:21]([CH3:26])[C:20]=2[CH2:27][S:28]([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)=[O:9])=[CH:15][C:14]=1[CH3:35]

Komponenten

3

Edukt 2

HCID 70297m-Chloroperbenzoic acidHCID 13316982(4'-Fluoro-3,3',5-trimethyl[1,1'-biphenyl]-2-YL)methyl phenyl sulfide

Produkt 1

HCID 13316983(4'-Fluoro-3,3',5-trimethyl-[1,1'-biphenyl]-2-yl-methyl)phenyl sulfoxideAusbeute 88 %

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

m-Chloroperbenzoic acid (tech. grade, approximately 75% peroxide; 1.19 g, approximately 5 mmoles) was added in small portions to a stirred solution of (4'-fluoro-3,3',5-trimethyl-[1,1'-biphenyl]-2-yl-methyl)phenyl sulfide (1.68 g, 5 mmoles) at -78° C. The reaction mixture was then stirred at -78° C. for 30 minutes and allowed to warm to room temperature. The solution of the product was separated by filtration from the 3-chlorobenzoic acid which was washed with methylene chloride. The combined methylene chloride solutions of the product were diluted with methylene chloride to 100 ml then washed with dilute sodium hydroxide solution (2×50 ml) dried (MgSO4), filtered, and the solvent was evaporated in vacuo to leave 1.7 g of crude product. This was purified by flash chromatography on silica gel using a 40×150 mm column eluting with 3.5% (v:v) acetone in methylene chloride to give 1.55 g of the title compound as a gum. Dry toluene was added and evaporated in vacuo four times to dry the product, which then crystallized, m.p. 75°-85° C.

Aufarbeitung

  1. temperatureto warm to room temperature
  2. customThe solution of the product was separated by filtration from the 3-chlorobenzoic acid which
  3. washwas washed with methylene chloride
  4. additionThe combined methylene chloride solutions of the product were diluted with methylene chloride to 100 ml
  5. washthen washed with dilute sodium hydroxide solution (2×50 ml)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent was evaporated in vacuo
  9. customto leave 1.7 g of crude product
  10. customThis was purified by flash chromatography on silica gel using a 40×150 mm column
  11. washeluting with 3.5% (v:v) acetone in methylene chloride

Quellen und Nachweise

ORD-Eintrag
ord-ad9d51402d8a41068ecf309517636482
Quelldatensatz
uspto-grants-1987_07
Patentnummer
US04683314

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