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

HRID 1473512ノート

反応式

HRID 1473512 の反応式
[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]

参加物

5

反応物 3

HCID 6342AcetonitrileHCID 24813Phosphorus oxychlorideHCID 178516369HCID 178516369、化合物

生成物 1

HCID 866875667-Bromo-4-chloro-6-fluoroquinoline収率 28.5%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
90 °C

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-e39c3ea282a648d2b6a1481f97a12130
出典データセット
uspto-grants-2015_04
特許番号
US09012443B2

反応ノート

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