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1,8-Diazabicyclo(5.4.0)undec-7-ene → 1-(Azidomethyl)-2,3-difluoro-5-methoxybenzene

HRID 1527454
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HRID 1527454 반응식
[F:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([O:9][CH3:10])=[CH:4][C:3]=1[CH2:11]O.C1C=CC(P([N:27]=[N+:28]=[N-:29])(C2C=CC=CC=2)=O)=CC=1.C1CCN2C(=NCCC2)CC1>C1(C)C=CC=CC=1.CCOC(C)=O>[N:27]([CH2:11][C:3]1[CH:4]=[C:5]([O:9][CH3:10])[CH:6]=[C:7]([F:8])[C:2]=1[F:1])=[N+:28]=[N-:29]
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참가 물질

6

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HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 682836852,3-Difluoro-5-methoxybenzenemethanol

생성물 1

HCID 866738621-(Azidomethyl)-2,3-difluoro-5-methoxybenzene

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8857Ethyl Acetate
용매

실험 절차

To a solution of (2,3-difluoro-5-methoxy-phenyl)-methanol (715 mg, 4.11 mmol) in toluene (10 mL) was added DPPA (1.04 mL, 4.93 mmol) and DBU (0.805 mL, 5.34 mmol), followed by stirring at RT for 1 h. The reaction mixture was diluted with EtOAc, the organics were washed with diluted brine (20 mL), dried (Phase separator) and evaporated in vacuo. The residue was purified by flash column chromatography on silica gel (c-hexane/EtOAc 9:1) to afford the title compound as a colorless oil. TLC Rf (c-hexane/EtOAc 3:1)=0.55; MS (LC/MS): 208.0 [M+NH4]+; tR (HPLC conditions c): 5.46 min.

후처리

  1. washthe organics were washed with diluted brine (20 mL)
  2. customdried (Phase separator)
  3. customevaporated in vacuo
  4. customThe residue was purified by flash column chromatography on silica gel (c-hexane/EtOAc 9:1)

출처 및 근거

ORD 기록
ord-65a79888782a4a11a234b687c6a26fcf
출처 데이터셋
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09085555B2

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