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

HRID 1532575
ノート
印刷プレビュー

反応式

HRID 1532575 の反応式
[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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 124181,1,1,2-TetrachloroethaneHCID 14798Sodium HydroxideHCID 24613Phosphorus oxybromideHCID 178481771HCID 178481771、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 3283
Diethyl Ether
溶媒

反応条件

温度
130 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-1f18caf9a05d4a5f9564df1615132eaa
出典データセット
uspto-grants-2001_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06204221B1

反応ノート

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