Acetonitrile → 7-Bromo-4-chloro-6-fluoroquinoline

HRID 1473512노트

반응식

HRID 1473512 반응식
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](O)=[CH:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[F:13].C(#N)C.P(Cl)(Cl)([Cl:19])=O>C(OCC)(=O)C>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([Cl:19])=[CH:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[F:13]

참가 물질

5

반응물 3

HCID 6342AcetonitrileHCID 24813Phosphorus oxychlorideHCID 178516369HCID 178516369, 화합물

생성물 1

HCID 866875667-Bromo-4-chloro-6-fluoroquinoline수율 28.5%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

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온도
90 °C

실험 절차

A vial was charged with 7-bromo-6-fluoroquinolin-4-ol (0.460 g, 1.900 mmol) and acetonitrile (9.50 ml). Phosphoryl trichloride (0.354 ml, 3.80 mmol) was then added, and the reaction was stirred for 2 h at 90° C. The reaction was diluted with ethyl acetate and washed with water. The aqueous was extracted once more with ethyl acetate, and the combined organics were dried over sodium sulfate, filtered and concentrated in vacuo. The material was then purified via silica gel chromatography eluting with 0-75% ethyl acetate in heptanes to yield 7-bromo-4-chloro-6-fluoroquinoline (0.141 g, 0.541 mmol, 28.5% yield) as a white solid. m/z (ESI) 260.1 (M+H)+.

후처리

  1. washwashed with water
  2. extractionThe aqueous was extracted once more with ethyl acetate
  3. dry with materialthe combined organics were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe material was then purified via silica gel chromatography
  7. washeluting with 0-75% ethyl acetate in heptanes

출처 및 근거

ORD 기록
ord-e39c3ea282a648d2b6a1481f97a12130
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09012443B2

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