Hydrogen Bromide → 3-Bromo-1-(4-fluorophenyl)-5-[4-(methylthio)phenyl]pyrazole

HRID 654803노트

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HRID 654803 반응식
N([O-])=O.[Na+].[F:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]2[C:16]([C:17]3[CH:22]=[CH:21][C:20]([S:23][CH3:24])=[CH:19][CH:18]=3)=[CH:15][C:14](N)=[N:13]2)=[CH:8][CH:7]=1.S(=O)(=O)(O)O.[Br-:31].[Na+].Br>O.C(#N)C>[Br:31][C:14]1[CH:15]=[C:16]([C:17]2[CH:22]=[CH:21][C:20]([S:23][CH3:24])=[CH:19][CH:18]=2)[N:12]([C:9]2[CH:10]=[CH:11][C:6]([F:5])=[CH:7][CH:8]=2)[N:13]=1

참가 물질

8

반응물 5

HCID 260Hydrogen BromideHCID 1118Sulfuric AcidHCID 253881Sodium BromideHCID 107565811-(4-Fluorophenyl)-5-[4-(methylthio)phenyl]-3-pyrazolamineHCID 23668193Sodium Nitrite

생성물 1

HCID 104989163-Bromo-1-(4-fluorophenyl)-5-[4-(methylthio)phenyl]pyrazole수율 28.8%

시약·촉매·용매 2

HCID 962Water용매3회HCID 6342Acetonitrile용매

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온도
0 °C

실험 절차

A solution of sodium nitrite (0.26 g) in water (0.3 ml) was added to an ice-salt cooled mixture of 1-(4-fluorophenyl)-5-[4-(methylthio)phenyl]-3-pyrazolamine (1 g), acetonitrile (1 ml), sulfuric acid (0.6 ml) and water (1.6 ml). The mixture was stirred at 0° C. for 30 minutes. The resulting mixture was added portionwise to a mixture of cuprous bromide (645 mg), sodium bromide (582 mg), hydrobromic acid (1.7 ml) and water (3 ml) at 80° C. The mixture was stirred at 80° C. for 30 minutes and extracted with toluene. The extract was washed with water, dried, and evaporated in vacuo. The obtained residue was purified by column chromatography on silica gel (10 g) to give crystals of 3-bromo-1-(4-fluorophenyl)-5-[4-(methylthio)phenyl]pyrazole (0.35 g).

후처리

  1. temperaturecooled
  2. stirringThe mixture was stirred at 80° C. for 30 minutes
  3. extractionextracted with toluene
  4. washThe extract was washed with water
  5. customdried
  6. customevaporated in vacuo
  7. customThe obtained residue was purified by column chromatography on silica gel (10 g)

출처 및 근거

ORD 기록
ord-1f43d160377141a1a4d09d4d0dd9aca5
출처 데이터셋
uspto-grants-1992_07
특허 번호
US05134142

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