3-Bromophenylhydrazine hydrochloride → ethyl 1-(3-bromophenyl)-5-tert-butyl-1H-pyrazole-3-carboxylate

HRID 733126

반응식

HRID 733126 반응식
Cl.[Br:2][C:3]1[CH:4]=[C:5]([NH:9][NH2:10])[CH:6]=[CH:7][CH:8]=1.[CH3:11][C:12]([CH3:24])([CH3:23])[C:13](=O)[CH2:14][C:15](=O)[C:16]([O:18][CH2:19][CH3:20])=[O:17]>C(O)(=O)C>[Br:2][C:3]1[CH:4]=[C:5]([N:9]2[C:13]([C:12]([CH3:11])([CH3:23])[CH3:24])=[CH:14][C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[N:10]2)[CH:6]=[CH:7][CH:8]=1

참가 물질

4

반응물 2

HCID 337573-Bromophenylhydrazine hydrochlorideHCID 83403Ethyl 5,5-dimethyl-2,4-dioxohexanoate

생성물 1

HCID 57428253ethyl 1-(3-bromophenyl)-5-tert-butyl-1H-pyrazole-3-carboxylate수율 76.4%

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

A solution of 3-bromophenylhydrazine hydrochloride (0.5 g, 2.2 mmol) and ethyl 5,5-dimethyl-2,4-dioxohexanoate (0.54 g, 2.68 mmol) in acetic acid (10 ml) was refluxed for 16 hours. The reaction was cooled to room temperature, and the solvent was removed under reduced pressure. The residue was partitioned between ethyl acetate and water. The organic layer was washed with water, saturated bicarbonate and brine, and dried over sodium sulfate, filtered and concentrated. The crude material was purified by column chromatography (4.8:0.2 hexanes/ethyl acetate) to give ethyl 1-(3-bromophenyl)-5-tert-butyl-1H-pyrazole-3-carboxylate (0.59 g, 74%) as a syrup.

후처리

  1. customthe solvent was removed under reduced pressure
  2. customThe residue was partitioned between ethyl acetate and water
  3. washThe organic layer was washed with water, saturated bicarbonate and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude material was purified by column chromatography (4.8:0.2 hexanes/ethyl acetate)

출처 및 근거

ORD 기록
ord-610ff5fafba24af88484ecb8caab413b
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07589116B2

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