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

HRID 2276314노트

반응식

HRID 2276314 반응식
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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
110 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-e70b975e41e245c1bdc2635464b2e199
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09132122B2

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