Dimethyl Sulfoxide → 2,6-Dichloropyridine-4-carbaldehyde

HRID 1590392Notes

Reaction equation

HRID 1590392 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8][OH:9])[CH:5]=[C:4]([Cl:10])[N:3]=1.C(Cl)(=O)C(Cl)=O.CS(C)=O>C(N(CC)CC)C>[Cl:1][C:2]1[CH:7]=[C:6]([CH:8]=[O:9])[CH:5]=[C:4]([Cl:10])[N:3]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 65578Oxalyl chlorideHCID 2794840(2,6-Dichloropyridin-4-yl)methanol

Product 1

HCID 27610242,6-Dichloropyridine-4-carbaldehydeYield 101.1%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Oxidation of the above alcohol (1.2 g) according to the conditions of Swern (oxalyl chloride, 0.33 ml; dimethyl sulphoxide, 0.54 ml; triethylamine, 2.35 ml) gave (2,6-dichloro-4-pyridyl)methanal (1.2 g). NMR 1H: 10.02(1H,s), 7.68(2H,s).

Sources & evidence

ORD record
ord-f0cf90c7d95b416782c027e4531301dd
Source dataset
uspto-grants-1993_04
Patent number
US05202356

Reaction notes

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