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

HRID 654803ノート

反応式

HRID 654803 の反応式
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

参加物

8

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒3 回HCID 6342Acetonitrile溶媒

反応条件

温度
0 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-1f43d160377141a1a4d09d4d0dd9aca5
出典データセット
uspto-grants-1992_07
特許番号
US05134142

反応ノート

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