Water → 4-Bromo-1-phenyl-1H-pyrazole

HRID 747927

反応式

HRID 747927 の反応式
[Br:1]Br.[C:3]1([N:9]2[CH:13]=[CH:12][CH:11]=[N:10]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.O.C([O-])(O)=O.[Na+]>C(O)(=O)C.C(OCC)(=O)C>[Br:1][C:12]1[CH:11]=[N:10][N:9]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:13]=1

参加物

7

反応物 4

HCID 962WaterHCID 24408BromineHCID 707691-PhenylpyrazoleHCID 516892Sodium Bicarbonate

生成物 1

HCID 7868114-Bromo-1-phenyl-1H-pyrazole収率 97%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒2 回HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

A solution of bromine (1.1 g, 6.94 mmol) in acetic acid (10 mL) was added to a mixture of 1-phenylpyrazole (Aldrich, 1 g, 6.94 mmol) in acetic acid (10 mL). This mixture was warmed to 100° C. in a pressure tube for 8 h. The material was cooled to ambient temperature, poured into ice and H2O neutralized with excess saturated, aqueous NaHCO3. Ethyl acetate (50 mL) was added and the layers were separated. The aqueous layer was extracted with EtOAc (2×15 mL) and the combined organic extract was dried over Na2SO4 and concentrated under reduced pressure to give a crude solid. Purification by column chromatography (SiO2, 50% hexanes-EtOAc) provided the title compound (1.5 g, 6.72 mmol, 97% yield). MS (DCl/NH3) m/z 223, 225 (M+H)+.

後処理

  1. temperatureThe material was cooled to ambient temperature
  2. customthe layers were separated
  3. extractionThe aqueous layer was extracted with EtOAc (2×15 mL)
  4. extractionthe combined organic extract
  5. dry with materialwas dried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customto give a crude solid
  8. customPurification by column chromatography (SiO2, 50% hexanes-EtOAc)

出典と根拠

ORDレコード
ord-c38252d273b14267be5fbc20209d98f2
出典データセット
uspto-grants-2008_07
特許番号
US07399765B2

関連ノート

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