Acetic Acid → (1-phenyl-1H-pyrazol-5-yl)boronic acid

HRID 333721

반응식

HRID 333721 반응식
[C:1]1([N:7]2[CH:11]=[CH:10][CH:9]=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([Li])CCC.[B:17](OC(C)C)([O:22]C(C)C)[O:18]C(C)C.C(O)(=O)C>O1CCCC1>[C:1]1([N:7]2[C:11]([B:17]([OH:22])[OH:18])=[CH:10][CH:9]=[N:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 21531Triisopropyl borateHCID 707691-PhenylpyrazoleHCID 178418339Butyllithium

생성물 1

HCID 59436217(1-phenyl-1H-pyrazol-5-yl)boronic acid수율 95.9%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 1-phenyl-1H-pyrazole (20.0 g) in tetrahydrofuran (700 mL) was added dropwise n-butyllithium (2.5M hexane solution, 58.3 mL) under a nitrogen atmosphere at −78° C., and the mixture was stirred at the same temperature for min. To the reaction mixture was added triisopropyl borate (52.2 g) at −78° C., and the mixture was stirred at the same temperature for 1 hr. The mixture was gradually warmed to room temperature, and stirred at room temperature for 20 hr. To the reaction mixture was added acetic acid (20 mL) to adjust to pH 5, and the mixture was concentrated to give the title compound (25.0 g).

후처리

  1. stirringthe mixture was stirred at the same temperature for 1 hr
  2. stirringstirred at room temperature for 20 hr
  3. concentrationthe mixture was concentrated

출처 및 근거

ORD 기록
ord-0ce174f833cc450e97e671a0493ec689
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08883788B2

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