Triphenylphosphine → 4-(Bromomethyl)-1-fluoro-2-(methylsulfonyl)benzene

HRID 1013991Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1013991
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:20]Br.[F:22][C:23]1[CH:28]=[CH:27][C:26]([CH2:29]O)=[CH:25][C:24]=1[S:31]([CH3:34])(=[O:33])=[O:32].C(=O)([O-])O.[Na+]>C(#N)C>[Br:20][CH2:29][C:26]1[CH:27]=[CH:28][C:23]([F:22])=[C:24]([S:31]([CH3:34])(=[O:33])=[O:32])[CH:25]=1

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 24408BromineHCID 516892Sodium BicarbonateHCID 668778384-Fluoro-3-(methylsulfonyl)benzenemethanol

Produkt 1

HCID 668776264-(Bromomethyl)-1-fluoro-2-(methylsulfonyl)benzene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

(Step 1) Triphenylphosphine (3.21 g) was suspended in acetonitrile (50 ml), bromine (0.64 ml) was added, and the mixture was stirred for 30 min. [4-Fluoro-3-(methylsulfonyl)phenyl]methanol (2.5 g) was added to the reaction mixture, and the mixture was stirred at 85° C. for 20 hr, treated with aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The obtained residue was purified by basic silica gel chromatography (ethyl acetate:hexane=1:1) to give 4-(bromomethyl)-1-fluoro-2-(methylsulfonyl)benzene (1.64 g).

Aufarbeitung

  1. additionwas added to the reaction mixture
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by basic silica gel chromatography (ethyl acetate:hexane=1:1)

Quellen und Nachweise

ORD-Eintrag
ord-1a5aa084d6f847bcaa2850dbf488dae9
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07982044B2

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