Water → 4-Bromo-1-phenyl-1H-pyrazole

HRID 253188

반응식

HRID 253188 반응식
[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

참가 물질

7

반응물 4

HCID 962WaterHCID 24408BromineHCID 707691-PhenylpyrazoleHCID 516892Sodium Bicarbonate

생성물 1

HCID 7868114-Bromo-1-phenyl-1H-pyrazole수율 97%

시약·촉매·용매 2

HCID 176Acetic Acid용매2회HCID 8857Ethyl Acetate용매

반응 조건

온도
100 °C

실험 절차

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)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-d61ee454aa6348f4b2eac242bece53a8
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07872010B2

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