Phosphorus oxybromide → 4-bromo-1-butylpyridin-2(1H)-one

HRID 516620ノート

反応式

HRID 516620 の反応式
P(Br)(Br)([Br:3])=O.[CH2:6]([N:10]1[CH:15]=[CH:14][C:13](O)=[CH:12][C:11]1=[O:17])[CH2:7][CH2:8][CH3:9]>CN(C=O)C>[Br:3][C:13]1[CH:14]=[CH:15][N:10]([CH2:6][CH2:7][CH2:8][CH3:9])[C:11](=[O:17])[CH:12]=1

参加物

4

反応物 2

HCID 24613Phosphorus oxybromideHCID 594970761-butyl-4-hydroxy-1H-pyridine-2-one

生成物 1

HCID 594970924-bromo-1-butylpyridin-2(1H)-one収率 93%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
110 °C

実験手順

Phosphorus oxybromide (5.4 g, 18.9 mmol) was added to a solution of intermediate D5 (1.44 g, 8.6 mmol) in DMF (140 ml) and the mixture was heated at 110° C. for 1 hour. After cooling in an ice bath, the solution was partitioned between water and EtOAc. After three extractions with EtOAc, the combined organic fractions were dried (Na2SO4) and the solvent evaporated in vacuo. The crude product was purified by column chromatography (silica gel; DCM as eluent). The desired fractions were collected and evaporated in vacuo to yield intermediate D6 (1.82 g, 93%).

後処理

  1. temperatureAfter cooling in an ice bath
  2. customthe solution was partitioned between water and EtOAc
  3. extractionAfter three extractions with EtOAc
  4. dry with materialthe combined organic fractions were dried (Na2SO4)
  5. customthe solvent evaporated in vacuo
  6. customThe crude product was purified by column chromatography (silica gel; DCM as eluent)
  7. customThe desired fractions were collected
  8. customevaporated in vacuo

出典と根拠

ORDレコード
ord-030ec2cc9bb84ba2b21ad726162d1b45
出典データセット
uspto-grants-2015_08
特許番号
US09114138B2

反応ノート

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