Hydrochloric Acid → (2-Fluoro-4-iodopyridin-3-yl)methanol

HRID 2401379Notes

Reaction equation

HRID 2401379 reaction equation
[F:1][C:2]1[N:9]=[CH:8][CH:7]=[C:6]([I:10])[C:3]=1[CH:4]=[O:5].[BH4-].[Na+].Cl>CCO>[F:1][C:2]1[C:3]([CH2:4][OH:5])=[C:6]([I:10])[CH:7]=[CH:8][N:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 99923282-Fluoro-4-iodopyridine-3-carbaldehyde

Product 1

HCID 11021396(2-Fluoro-4-iodopyridin-3-yl)methanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-fluoro-4-iodonicotinaldehyde (3.50 g, 13.94 mmol) in absolute EtOH (56 mL) was added sodium borohydride (0.264 g, 6.97 mmol) at room temperature. The reaction was stirred at room temperature for 1 h, followed by the slow addition of 1 M aqueous hydrochloric acid. The product was extracted with CH2Cl2 (repeated four times), and the organic layers were combined, dried over sodium sulfate, filtered and concentrated to dryness. The aqueous phase was basified to pH 8-10 with 2 M aqueous sodium hydroxide and extracted with diethylether (repeated four times). Then the organic layers were combined, dried over sodium sulfate, filtered, combined with the previously obtained residue and concentrated to dryness under vacuum. The residue was used without any purification in the next step. LC/MS m/z 254 [M+H]+.

Workup

  1. extractionThe product was extracted with CH2Cl2 (repeated four times)
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated to dryness
  5. extractionextracted with diethylether (repeated four times)
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated to dryness under vacuum
  9. customThe residue was used without any purification in the next step

Sources & evidence

ORD record
ord-a4c996ba723448529938276e5570831a
Source dataset
uspto-grants-2014_08
Patent number
US08796261B2

Reaction notes

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