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

HRID 448807
Notes
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Reaction equation

HRID 448807 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[C:12]([P:15](=[O:22])([O:19][CH2:20][CH3:21])[O:16][CH2:17][CH3:18])([F:14])[F:13])[N:8]=[C:7](/[CH:23]=[N:24]/O)[CH:6]=[CH:5]2.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)(Cl)Cl>C(#N)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[C:12]([P:15](=[O:22])([O:16][CH2:17][CH3:18])[O:19][CH2:20][CH3:21])([F:14])[F:13])[N:8]=[C:7]([C:23]#[N:24])[CH:6]=[CH:5]2
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6342Acetonitrile
Solvent

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

  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%)

Sources & evidence

ORD record
ord-80b0741113f04c1b9567ea9611b45fd5
Source dataset
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08481742B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes