8-Methoxypsoralen → 4-Bromo-9-methoxy-7h-furo[3,2-g]chromen-7-one

HRID 36837

Reaktionsgleichung

Reaktionsgleichung von HRID 36837
[CH3:1][O:2][C:3]1[C:11]2[O:12][C:13]([CH:15]=[CH:16][C:10]=2[CH:9]=[C:5]2[CH:6]=[CH:7][O:8][C:4]=12)=[O:14].[Br:17]Br.S([O-])([O-])(=O)=S.[Na+].[Na+].[NH4+].[OH-]>O1CCCC1>[CH3:1][O:2][C:3]1[C:11]2[O:12][C:13]([CH:15]=[CH:16][C:10]=2[C:9]([Br:17])=[C:5]2[CH:6]=[CH:7][O:8][C:4]=12)=[O:14]

Komponenten

6

Edukt 4

HCID 41148-MethoxypsoralenHCID 14923Ammonium HydroxideHCID 24408BromineHCID 24477Sodium Thiosulfate

Produkt 1

HCID 2400484-Bromo-9-methoxy-7h-furo[3,2-g]chromen-7-oneAusbeute 73,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

8-methoxypsoralen (8-MOP, Aldrich, Milwaukee, Wis., 0.75 g, 3.5 m mol) was dissolved in tetrahydrofuran (THF, 75 mL), Bromine (1.5 mL, 3.5 mmol) in THF (5 mL) was added dropwise. The resulting mixture was stirred at room temperature for overnight. 10% Sodium thiosulfate (5 mL) was added and the solution was basified using conc. aqueous NH4OH, and then extracted twice with chloroform. The organic layer was recrystallized from chloroform to give the product 5-bromo-8-methoxypsoralen (0.75 g, 73.5% yield).

Aufarbeitung

  1. extractionextracted twice with chloroform
  2. customThe organic layer was recrystallized from chloroform

Quellen und Nachweise

ORD-Eintrag
ord-32f0189489ac4c28bee24628766de52c
Quelldatensatz
uspto-grants-1995_05
Patentnummer
US05418130

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