Methanol → 3,5-Dichloro-2,6-difluoropyridine-4-carbaldehyde

HRID 256166Notes

Reaction equation

HRID 256166 reaction equation
[C:1]([C:3]1[C:8]([Cl:9])=[C:7]([F:10])[N:6]=[C:5]([F:11])[C:4]=1[Cl:12])#N.[H-].C([Al+]CC(C)C)C(C)C.CO.S(=O)(=O)(O)[OH:26]>C1(C)C=CC=CC=1>[Cl:12][C:4]1[C:5]([F:11])=[N:6][C:7]([F:10])=[C:8]([Cl:9])[C:3]=1[CH:1]=[O:26]

Participants

6

Reactant 4

HCID 887MethanolHCID 1118Sulfuric AcidHCID 139851654-Cyano-3,5-dichloro-2,6-difluoropyridineHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 27630053,5-Dichloro-2,6-difluoropyridine-4-carbaldehyde

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a mixture, of 10.1 g (0.048 mole) of 4-cyano-3,5-dichloro-2,6-difluoropyridine (from Step A) in 50 ml of toluene that had been cooled to 0° C. was added 6.9 g (0.049 mole) of diisobutylaluminum hydride. After complete addition the reaction mixture was allowed to warm to room temperature and was stirred for approximately seventeen hours. A mixture of methanol and petroleum ether (2:1) was added to the reaction mixture which was then acidified with dilute sulfuric acid. The organic layer was separated from the aqueous layer and was dried over anhydrous sodium sulfate. After being filtered, the solvent was evaporated under reduced pressure, leaving 6.0 g of 3,5-dichloro-2,6-difluoropyridine-4-carboxaldehyde as a residue.

Workup

  1. additionAfter complete addition the reaction mixture
  2. additionwas added to the reaction mixture which
  3. customThe organic layer was separated from the aqueous layer
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. filtrationAfter being filtered
  6. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-5dd26199596841349d7b256f34b1339a
Source dataset
uspto-grants-1987_10
Patent number
US04701464

Reaction notes

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