Ethyl Bromide → Fluoresone

HRID 238587

Reaktionsgleichung

Reaktionsgleichung von HRID 238587
P([O-])([O-])(O)=O.[Na+].[Na+].S([O-])([O-])=O.[Na+].[Na+].[F:14][C:15]1[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1.Br[CH2:26][CH3:27]>O.CC(C)=O.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:26]([S:21]([C:18]1[CH:19]=[CH:20][C:15]([F:14])=[CH:16][CH:17]=1)(=[O:23])=[O:22])[CH3:27]

Komponenten

8

Edukt 4

HCID 6332Ethyl BromideHCID 95884-Fluorobenzenesulfonyl chlorideHCID 24203Sodium Phosphate, DibasicHCID 24437Sodium Sulfite

Produkt 1

HCID 71814FluoresoneAusbeute 63,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 67553Tetrabutylammonium IodideKatalysatorHCID 180AcetoneLösungsmittelHCID 962WaterLösungsmittel2×

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of sodium hydrogen phosphate (14.2 g, 0.1 mol) and sodium sulfite (25.2 g, 0.2 mol) in water (200 mL) was added 4-fluoro-benzenesulfonyl chloride (19.5 g, 0.1 mol). After the mixture was stirred at 60° C. overnight, a solution of bromoethane (32.7 g, 0.3 mol) in acetone (20 mL) was added dropwise, followed by the addition of tetrabutylammonium iodide (3.7 g, 0.01 mol) in one portion. The resulting reaction mixture was stirred at room temperature for 5 days, then diluted with water (50 mL), and extracted with ethyl acetate (100 mL×3). The combined organic layers were washed with brine, dried over sodium sulfate, and concentrated in vacuo. The residue was purified by flash column chromatography (elution with 20% ethyl acetate in petroleum ether) to afford 1-ethanesulfonyl-4-fluoro-benzene (11.9 g, 63%) as a yellow oil (reference: Arnold, Leggy A. A., et al., Org. Lett, 6 (2004), 3005-3007).

Aufarbeitung

  1. customThe resulting reaction mixture
  2. stirringwas stirred at room temperature for 5 days
  3. extractionextracted with ethyl acetate (100 mL×3)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash column chromatography (elution with 20% ethyl acetate in petroleum ether)

Quellen und Nachweise

ORD-Eintrag
ord-7c0ad6e0853241309521ef6621b24da2
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642629B2

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