Sulfuric Acid → 6-Bromo-5,7-difluoroquinoline

HRID 655218

反応式

HRID 655218 の反応式
[Br:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([NH2:9])=[CH:4][C:3]=1[F:10].[N+]([C:14]1[CH:19]=CC=C[CH:15]=1)([O-])=O.S(=O)(=O)(O)O>OCC(CO)O>[Br:1][C:2]1[C:7]([F:8])=[C:6]2[C:5](=[CH:4][C:3]=1[F:10])[N:9]=[CH:19][CH:14]=[CH:15]2

参加物

5

反応物 3

HCID 1118Sulfuric AcidHCID 7416NitrobenzeneHCID 27362604-Bromo-3,5-difluoroaniline

生成物 1

HCID 451083546-Bromo-5,7-difluoroquinoline

試薬・触媒・溶媒 1

HCID 753Glycerol溶媒

実験手順

A mixture of 4-bromo-3,5-difluoro-phenylamine (6.0 g, 28.8 mmole), ferrous sulfate (1.82 g), glycerol (8.6 mL), nitrobenzene (1.79 mL) and 5.0 ml of concentrated sulfuric acid (5 mL) was heated gently. After the first vigorous reaction, the mixture was heated to reflux for five hours. Nitrobenzene was removed by distillation in vacuo. The aqueous solution was acidified with glacial acetic acid, and dark brown precipitate separated, which was purified by flash chromatography (silica gel, petroleum/ethyl acetate=12/1) to return the title compound as a white solid (3.5 g, 49.8%).

後処理

  1. temperaturewas heated gently
  2. customAfter the first vigorous reaction
  3. temperaturethe mixture was heated
  4. temperatureto reflux for five hours
  5. customNitrobenzene was removed by distillation in vacuo
  6. customseparated
  7. customwhich was purified by flash chromatography (silica gel, petroleum/ethyl acetate=12/1)

出典と根拠

ORDレコード
ord-1a35cf78a93446f093396b06b5071da6
出典データセット
uspto-grants-2011_12
特許番号
US08071581B2

関連ノート

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