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

HRID 1422584Notes

Reaction equation

[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]

Participants

Conditions

Temperature: 100 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-f9cac2bc9f2b44329eaee9ff4e4da441
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08927526B2

Reaction notes

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