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Carbon Tetrachloride → Diethyl[(6-bromo-2-cyanoquinolin-7-yl)(difluoro)methyl]phosphonate

HRID 1422584
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HRID 1422584 반응식
[CH2:1]([O:3][P:4]([C:9]([C:12]1[CH:21]=[C:20]2[C:15]([CH:16]=[CH:17][C:18](/[CH:22]=[N:23]/O)=[N:19]2)=[CH:14][C:13]=1[Br:25])([F:11])[F:10])(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)(Cl)Cl>C(#N)C>[CH2:1]([O:3][P:4]([C:9]([C:12]1[CH:21]=[C:20]2[C:15]([CH:16]=[CH:17][C:18]([C:22]#[N:23])=[N:19]2)=[CH:14][C:13]=1[Br:25])([F:10])[F:11])(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2]
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참가 물질

5

반응물 3

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 136390154(NE)-N-[[6-bromo-7-[diethoxyphosphoryl(difluoro)methyl]quinolin-2-yl]methylidene]hydroxylamine

생성물 1

HCID 86638326Diethyl[(6-bromo-2-cyanoquinolin-7-yl)(difluoro)methyl]phosphonate

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
100 °C

실험 절차

To a stirred solution of diethyl[(6-bromo-2-[(E)-(hydroxyimino)methyl]quinolin-7-yl)(difluoro)methyl]phosphonate (520 mg, 1.189 mmol) in acetonitrile (30 mL) at room temperature were added triphenylphosphine (1.248 g, 4.76 mmol) and carbon tetrachloride (230 μL, 2.383 mmol). The reaction mixture was stirred at 100° C. for 1 hour. It was concentrated to dryness in vacuo, pre-adsorbed in silica gel for flash chromatography eluting with ethyl acetate in toluene (20% to 30%) to afford diethyl[(6-bromo-2-cyanoquinolin-7-yl)(difluoro)methyl]phosphonate.

후처리

  1. concentrationIt was concentrated to dryness in vacuo, pre-adsorbed in silica gel for flash chromatography
  2. washeluting with ethyl acetate in toluene (20% to 30%)

출처 및 근거

ORD 기록
ord-f9cac2bc9f2b44329eaee9ff4e4da441
출처 데이터셋
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08927526B2

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