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1,1,1,2-Tetrachloroethane → 3-(3-Fluoro-5-chloro-2-pyridyl)-5-bromo-1-methyl-[1H]-pyrazole

HRID 1532575
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HRID 1532575 반응식
[F:1][C:2]1[C:3]([C:9]2[CH:13]=[C:12](O)[N:11]([CH3:15])[N:10]=2)=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1.ClCC(Cl)(Cl)Cl.P(Br)(Br)([Br:24])=O.[OH-].[Na+]>C(OCC)C>[F:1][C:2]1[C:3]([C:9]2[CH:13]=[C:12]([Br:24])[N:11]([CH3:15])[N:10]=2)=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1
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참가 물질

6

반응물 4

HCID 124181,1,1,2-TetrachloroethaneHCID 14798Sodium HydroxideHCID 24613Phosphorus oxybromideHCID 178481771HCID 178481771, 화합물

생성물 1

HCID 217121223-(3-Fluoro-5-chloro-2-pyridyl)-5-bromo-1-methyl-[1H]-pyrazole수율 78.1%

시약·촉매·용매 1

HCID 3283
Diethyl Ether
용매

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온도
130 °C

실험 절차

20.0 g of 3-(3-fluoro-5-chloro-2-pyridyl)-5-hydroxy-1-methyl-[1H]-pyrazole (Example H14) are initially introduced into 80 ml of tetrachloroethane. A total of 25.2 g of phosphorus oxybromide (POBr3) are added in portions to the brown suspension and the mixture is then stirred at a temperature of 130° C. for 2 hours. Thereafter, it is cooled and 150 ml of a 2 molar sodium hydroxide solution are added dropwise, while cooling with an ice-bath. After addition of diethyl ether and separation of the phases, the organic phase is washed successively with water, dilute hydrochloric acid and brine, dried over sodium sulfate, filtered and concentrated in vacuo. 19.94 g of a brown solid are obtained as the crude product, and this solid is purified by means of digestion with 50 ml of n-hexane. 12.65 g of the desired title compound are obtained as a brown solid of melting point 110-111° C.

후처리

  1. temperatureThereafter, it is cooled
  2. temperaturewhile cooling with an ice-bath
  3. washthe organic phase is washed successively with water, dilute hydrochloric acid and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-1f18caf9a05d4a5f9564df1615132eaa
출처 데이터셋
uspto-grants-2001_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06204221B1

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