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

HRID 36837노트

반응식

HRID 36837 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-32f0189489ac4c28bee24628766de52c
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05418130

반응 노트

불러오는 중…