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

HRID 733126

反応式

HRID 733126 の反応式
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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-610ff5fafba24af88484ecb8caab413b
出典データセット
uspto-grants-2009_09
特許番号
US07589116B2

関連ノート

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