Ethanol → Ethyl 2-bromo-5-fluoroisonicotinate

HRID 1468290ノート

反応式

HRID 1468290 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([C:8]([F:11])=[CH:9][N:10]=1)[C:5]([OH:7])=[O:6].S(Cl)(Cl)=O.[CH2:16](O)[CH3:17]>>[Br:1][C:2]1[CH:3]=[C:4]([C:8]([F:11])=[CH:9][N:10]=1)[C:5]([O:7][CH2:16][CH3:17])=[O:6]

参加物

4

反応物 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 467392772-Bromo-5-fluoroisonicotinic acid

生成物 1

HCID 46311464Ethyl 2-bromo-5-fluoroisonicotinate収率 77%

実験手順

2-Bromo-5-fluoroisonicotinic acid (500 mg, 2.27 mmol) was dissolved in ethanol (22.7 mL), and the solution was stirred under heat and reflux for 1 hour after adding thionyl chloride (0.829 mL, 11.3 mmol). The solvent was then evaporated under reduced pressure. The residue was extracted with chloroform after adding a sodium hydrogen carbonate aqueous solution. The organic layer was dried over anhydrous sodium sulfate, and the solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=100/0→4/1) to give ethyl 2 bromo-5-fluoroisonicotinate (434 mg, yield 77%).

後処理

  1. temperatureunder heat
  2. temperaturereflux for 1 hour
  3. customThe solvent was then evaporated under reduced pressure
  4. extractionThe residue was extracted with chloroform
  5. additionafter adding a sodium hydrogen carbonate aqueous solution
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. customthe solvent was then evaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=100/0→4/1)

出典と根拠

ORDレコード
ord-ac02983a5d6149529059e35935b2f377
出典データセット
uspto-grants-2015_04
特許番号
US09000186B2

反応ノート

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