Bromine → Methyl 5-bromo-2-methylfuran-3-carboxylate

HRID 9634

反応式

HRID 9634 の反応式
[Br:1]Br.[CH3:3][C:4]1[O:5][CH:6]=[CH:7][C:8]=1[C:9]([O:11][CH3:12])=[O:10].S([O-])([O-])(=O)=S.[Na+].[Na+]>O1CCOCC1>[Br:1][C:6]1[O:5][C:4]([CH3:3])=[C:8]([C:9]([O:11][CH3:12])=[O:10])[CH:7]=1

参加物

5

反応物 3

HCID 24408BromineHCID 24477Sodium ThiosulfateHCID 80237Methyl 2-methylfuran-3-carboxylate

生成物 1

HCID 15534190Methyl 5-bromo-2-methylfuran-3-carboxylate

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
0 °C

実験手順

Bromine (2.0 ml) was added drop-wise to a mixture of methyl 2-methyl-3-furancarboxylate (5.0 g) in 1,4-dioxane (35 ml) stirred at 0° C. Stirring was continued at 0° C. for 2 hours and then at ambient temperature for 18 hours. Saturated aqueous sodium thiosulfate was added to the reaction mixture which was then extracted with ethyl acetate. The organic layer was dried with brine and over magnesium sulfate. The product isolated after evaporation of the solvent was further purified by flash column chromatography using cyclohexane:ethyl acetate (19:1) as eluent to give the title compound as a yellow oil.

後処理

  1. stirringStirring
  2. waitat ambient temperature for 18 hours
  3. extractionwas then extracted with ethyl acetate
  4. dry with materialThe organic layer was dried with brine and over magnesium sulfate
  5. customThe product isolated
  6. customafter evaporation of the solvent
  7. customwas further purified by flash column chromatography

出典と根拠

ORDレコード
ord-f33b834f86d64fcebdaf4b4e0d91a9c5
出典データセット
uspto-grants-2006_08
特許番号
US07091237B2

関連ノート

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