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

HRID 1920527Notes

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-3e7746eecdd94b00a773e9f3ced6490f
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08168815B2

Reaction notes

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