Phosphorodichloridic acid, phenyl ester → 2-Chloro-5-iodo-3-nitropyridine

HRID 733661Notes

Reaction equation

HRID 733661 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[C:5](O)=[N:6][CH:7]=1.C(=O)([O-])O.[Na+].P(Cl)([Cl:26])(OC1C=CC=CC=1)=O>CCCC(C)C>[Cl:26][C:5]1[C:4]([N+:9]([O-:11])=[O:10])=[CH:3][C:2]([I:1])=[CH:7][N:6]=1

Participants

5

Reactant 3

HCID 13038Phosphorodichloridic acid, phenyl esterHCID 516892Sodium BicarbonateHCID 178526737HCID 178526737, compound

Product 1

HCID 15142942-Chloro-5-iodo-3-nitropyridine

Reagents, catalysts & solvents 1

HCID 78922-MethylpentaneSolvent

Conditions

Temperature
180 °C

Procedure

A suspension of 5-iodo-3-nitro-pyridin-2-ol (20 g) in phenyl dichlorophosphate (60 ml) was heated at 180° C. for 30 minutes whereby a brown solution was obtained. The solution was allowed to cool then poured onto ice/water, neutralised by a portionwise addition of solid sodium hydrogen carbonate and extracted with ethyl acetate (300 ml) which was then washed twice with 5% sodium hydrogen carbonate solution (250 ml). The organic layer was dried (MgSO4), and evaporated to give a pale brown solid. The solid was stirred in isohexane for 2 h, filtered off, washed with isohexane and dried to afford the title compound (18.4 g).

Workup

  1. customwas obtained
  2. temperatureto cool
  3. additionthen poured onto ice/water
  4. extractionextracted with ethyl acetate (300 ml) which
  5. washwas then washed twice with 5% sodium hydrogen carbonate solution (250 ml)
  6. dry with materialThe organic layer was dried (MgSO4)
  7. customevaporated
  8. customto give a pale brown solid
  9. filtrationfiltered off
  10. washwashed with isohexane
  11. customdried

Sources & evidence

ORD record
ord-8f33821209674fdd905edde04500e113
Source dataset
uspto-grants-2009_09
Patent number
US07589206B2

Reaction notes

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