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

HRID 655218

반응식

HRID 655218 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

HCID 451083546-Bromo-5,7-difluoroquinoline

시약·촉매·용매 1

HCID 753Glycerol용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-1a35cf78a93446f093396b06b5071da6
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08071581B2

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