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

HRID 650485
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HRID 650485 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 P13) are introduced into 80 ml of tetrachloroethane. A total of 25.2 g of phosphorus oxybromide (POBr3) is added in portions to the brown suspension. The mixture is then stirred for 2 hours at an internal temperature of 130° C., after which it is cooled and, with cooling with an ice-bath, 150 ml of a 2M sodium hydroxide solution are added dropwise. After the addition of diethyl ether and separation of the phases, the organic phase is washed in succession with water, dilute hydrochloric acid and brine, dried over sodium sulfate, filtered and concentrated to dryness in vacuo. 19.94 g of a brown solid (crude product) are obtained, which is purified by means of digestion with 50 ml of n-hexane. 12.65 g of the desired compound are obtained in the form of a brown solid having a melting point of 110-111° C.

후처리

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

출처 및 근거

ORD 기록
ord-aeff02ef1fb2438ea6c661311cbfd03c
출처 데이터셋
uspto-grants-2001_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06274536B1

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