HCID 58443299, compound → HCID 58443273, compound

HRID 1630752Notes

Reaction equation

HRID 1630752 reaction equation
[Cl:1][C:2]1[C:3]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=2)=[CH:4][C:5]([CH2:8][OH:9])=[N:6][CH:7]=1>ClCCl.[O-2].[O-2].[Mn+4]>[Cl:1][C:2]1[C:3]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=2)=[CH:4][C:5]([CH:8]=[O:9])=[N:6][CH:7]=1

Participants

4

Reactant 1

HCID 58443299HCID 58443299, compound

Product 1

HCID 58443273HCID 58443273, compound

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (5-chloro-4-(3-fluorophenyl)pyridin-2-yl)methanol (0.138 g, 0.58 mmol) in dichloromethane (5 mL) at room temperature was added manganese dioxide (0.49 g, 5.6 mmol). The reaction mixture was stirred at room temperature for 3 d, filtered, and concentrated. Purification by flash column chromatography on silica gel (10% to 20% EtOAc in hexanes) gave 5-chloro-4-(3-fluorophenyl)picolinaldehyde.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. customPurification by flash column chromatography on silica gel (10% to 20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-1017b256d67948798dd3904772b46bd1
Source dataset
uspto-grants-2014_07
Patent number
US08791147B2

Reaction notes

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