Phosphorus oxychloride → 2-Chloro-3-iodo-5-nitropyridine

Reaction equation

[I:1][C:2]1[C:3](O)=[N:4][CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1.P(Cl)(Cl)([Cl:14])=O>>[Cl:14][C:3]1[C:2]([I:1])=[CH:7][C:6]([N+:8]([O-:10])=[O:9])=[CH:5][N:4]=1

Participants

Reactant 2

HCID 24813Phosphorus oxychloride

HCID 178526840HCID 178526840, compound

Product 1

HCID 111406392-Chloro-3-iodo-5-nitropyridine

Procedure

3-Iodo-5-nitropyridin-2-ol (3.00 g, 0.0113 mol) was heated to reflux in phosphoryl chloride (15 mL, 0.1609 mol) for 4 hours. The reaction was quenched in ice/water and was neutralized with Na2CO3. The reaction was extracted with ethyl acetate and the organic extracts were washed with water, saturated NaCl, dried (MgSO4) and stripped in vacuo to give the product, which was used in the next reaction without purification.

Workup

customThe reaction was quenched in ice/water
extractionThe reaction was extracted with ethyl acetate
washthe organic extracts were washed with water, saturated NaCl
dry with materialdried (MgSO4)
customto give the product, which
customwas used in the next reaction without purification

Sources & evidence

ORD record: ord-4f25e1129fd24f0cb896bcefa30ff55b
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08841318B2

Reaction notes

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