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

HRID 635149Notes

Reaction equation

HRID 635149 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

HCID 2400484-Bromo-9-methoxy-7h-furo[3,2-g]chromen-7-oneYield 73.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

8-methoxypsoralen (8-MOP, Aldrich, Milwaukee, Wis., 0.75 g, 3.5 mmol) 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).

Workup

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

Sources & evidence

ORD record
ord-fdf678b5afe04bf8a8b0eadfaf81ea50
Source dataset
uspto-grants-2001_02
Patent number
US06187572B1

Reaction notes

Loading…