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

HRID 1081962ノート

反応式

HRID 1081962 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-8137fdecf385472fbbe30c2941b4b38b
出典データセット
uspto-grants-1996_12
特許番号
US05587490

反応ノート

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