(5-Chloro-6-iodo-3-pyridinyl)methanol → 5-Chloro-6-iodo-3-pyridinecarbaldehyde

HRID 420746Notes

Reaction equation

HRID 420746 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][OH:10])[CH:5]=[N:6][C:7]=1[I:8]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[O:10])[CH:5]=[N:6][C:7]=1[I:8]

Participants

3

Reactant 1

HCID 58001734(5-Chloro-6-iodo-3-pyridinyl)methanol

Product 1

HCID 580017995-Chloro-6-iodo-3-pyridinecarbaldehydeYield 67.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of (5-chloro-6-iodo-3-pyridinyl)methanol (392 mg, 1.455 mmol), CrO2 (Magtrieve) (2.444 g, 29.1 mmol), and DCM (20 ml) was stirred at 40° C. for 24 h. Some starting material was still observed by TLC. More CrO2 (0.61 g) was added and the suspension stirred at 40° C. overnight. TLC showed full conversion. Filtration and concentration afforded 5-chloro-6-iodo-3-pyridinecarbaldehyde (261 mg, 67%) as a brown solid pure enough to be used in the next step.

Workup

  1. stirringthe suspension stirred at 40° C. overnight
  2. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-c9d6243951e74a7da4c97f7b3501fed7
Source dataset
uspto-grants-2012_01
Patent number
US08097628B2

Reaction notes

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