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Boron tribromide → 2-(4-Hydroxyphenyl)-5-methyl-2H-pyrazole-3-carboxylic acid ethyl ester

HRID 598779
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반응식

HRID 598779 반응식
[CH2:1]([O:3][C:4]([C:6]1[N:7]([C:12]2[CH:17]=[CH:16][C:15]([O:18]C)=[CH:14][CH:13]=2)[N:8]=[C:9]([CH3:11])[CH:10]=1)=[O:5])[CH3:2].B(Br)(Br)Br>C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[N:7]([C:12]2[CH:13]=[CH:14][C:15]([OH:18])=[CH:16][CH:17]=2)[N:8]=[C:9]([CH3:11])[CH:10]=1)=[O:5])[CH3:2]
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참가 물질

4

반응물 2

HCID 25134Boron tribromideHCID 11021617Ethyl 1-(4-methoxyphenyl)-3-methyl-1H-pyrazole-5-carboxylate

생성물 1

HCID 589487762-(4-Hydroxyphenyl)-5-methyl-2H-pyrazole-3-carboxylic acid ethyl ester수율 67.7%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
-40 °C

실험 절차

To a solution of 2-(4-methoxyphenyl)-5-methyl-2H-pyrazole-3-carboxylic acid ethyl ester (200 mg, 0.768 mmol, Example 10, Step 1) in methylene chloride (10 mL) at −40° C. was added boron tribromide (2.3 mL). The reaction was allowed to stir for 1 hour at −40° C. and for an additional hour while warming to room temperature. The reaction was quenched with ethanol diluted with water and methylene chloride. The organic layer was dried (MgSO4) and concentrated to give 128 mg of the desired product. LC-MS (C13H14N2O3 calculated 246) m/z 247 (M+H).

후처리

  1. temperaturewhile warming to room temperature
  2. customThe reaction was quenched with ethanol
  3. additiondiluted with water and methylene chloride
  4. dry with materialThe organic layer was dried (MgSO4)
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-e0caf069db084b379646ae21254c8d78
출처 데이터셋
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07897634B2

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