Propargyl bromide → 4-Chloro-1-(2,4-dichloro-5-prop-2-ynoxyphenyl)-3,5-dimethylpyrazole

HRID 580264노트

반응식

HRID 580264 반응식
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([OH:9])=[CH:4][C:3]=1[N:10]1[C:14]([CH3:15])=[C:13]([Cl:16])[C:12]([CH3:17])=[N:11]1.[CH2:18](Br)[C:19]#[CH:20].C[O-].[Na+].[Na]>C1(C)C=CC=CC=1.O.CO>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][CH2:20][C:19]#[CH:18])=[CH:4][C:3]=1[N:10]1[C:14]([CH3:15])=[C:13]([Cl:16])[C:12]([CH3:17])=[N:11]1

참가 물질

8

반응물 4

HCID 7842Propargyl bromideHCID 5360545SodiumHCID 10942334Sodium MethoxideHCID 13798309HCID 13798309, 화합물

생성물 1

HCID 1846184-Chloro-1-(2,4-dichloro-5-prop-2-ynoxyphenyl)-3,5-dimethylpyrazole수율 91.2%

시약·촉매·용매 3

HCID 887Methanol용매HCID 962Water용매HCID 1140Toluene용매2회

실험 절차

1-(2,4-dichloro-5-hydroxyphenyl)-3,5-dimethyl-4-chloropyrazole (29.2 g) and propargyl bromide (12.0 g) were added to a solution of sodium methoxide which was previously prepared from metallic sodium (2.3 g) and methanol (200 ml). The resulting mixture was heated under reflux, with stirring for 3 hours. To the reaction mixture, after cooling, were added water and toluene to form two layers. The toluene layer as formed was separated, washed with water and then dried over anhydrous sodium sulfate. Removal of the solvent by distillation in vacuo gave the titled compound (30.1 g) as a pale brown crystalline solid. Recrystallization of this solid from a mixture of cyclohexane/acetone afforded a white crystalline solid. m.p. 156.5°-158° C.

후처리

  1. temperatureThe resulting mixture was heated
  2. temperatureunder reflux
  3. temperatureTo the reaction mixture, after cooling
  4. customto form two layers
  5. customwas separated
  6. washwashed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. customRemoval of the solvent
  9. distillationby distillation in vacuo

출처 및 근거

ORD 기록
ord-829d181ad0bd40dfb73e4697ba444424
출처 데이터셋
uspto-grants-1988_06
특허 번호
US04752326

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