m-Chloroperbenzoic acid → 2-Fluoro-6-[(3-methoxyphenyl)sulfinyl]benzonitrile

HRID 839

Reaktionsgleichung

Reaktionsgleichung von HRID 839
[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([S:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=2)[C:3]=1[C:4]#[N:5].ClC1C=CC=C(C(OO)=[O:27])C=1.S(=O)(O)[O-].[Na+]>O>[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([S:10]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=2)=[O:27])[C:3]=1[C:4]#[N:5]

Komponenten

5

Edukt 3

HCID 70297m-Chloroperbenzoic acid2×HCID 107064062-Fluoro-6-[(3-methoxyphenyl)thio]benzonitrileHCID 23665763Sodium Bisulfite

Produkt 1

HCID 107787732-Fluoro-6-[(3-methoxyphenyl)sulfinyl]benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of 2 g (7.7 mmol) of 2-fluoro-6-[(3-methoxyphenyl)thio]benzonitrile (Example 13) was added portionwise 1.6 g (9.3 mmol) of m-chloroperbenzoic acid. The resultant mixture was stirred for 24 h. Additional 0.16 g of m-chloroperbenzoic acid was added and the resultant mixture was stirred for 15 min. Excess sodium bisulfite was added, followed by water. The H2O solution was extracted with EtOAc. After drying over MgSO4 and solvent removal, the resultant crude product was purified by flash column chromatography on silica gel with methylene chloride as the eluent. This resulted in 1.7 g of 2-fluoro-6-[(3-methoxyphenyl)sulfinyl]benzonitrile as a solid: mp 103°-111° C.

Aufarbeitung

  1. extractionThe H2O solution was extracted with EtOAc
  2. dry with materialAfter drying over MgSO4 and solvent removal
  3. customthe resultant crude product was purified by flash column chromatography on silica gel with methylene chloride as the eluent
  4. customThis resulted in 1.7 g of 2-fluoro-6-[(3-methoxyphenyl)sulfinyl]benzonitrile as a solid

Quellen und Nachweise

ORD-Eintrag
ord-f52f628e55bf48349560d5f7350120df
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05723452

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