Hydrochloric Acid → 1-(6-Fluoro-4-iodo-pyridin-3-yl)-ethanol

HRID 1640880Notes

Reaction equation

HRID 1640880 reaction equation
Cl.[F:2][C:3]1[CH:8]=[C:7]([I:9])[C:6]([CH:10]([O:12]COC)[CH3:11])=[CH:5][N:4]=1>CO.C(=O)([O-])[O-].[Na+].[Na+]>[F:2][C:3]1[N:4]=[CH:5][C:6]([CH:10]([OH:12])[CH3:11])=[C:7]([I:9])[CH:8]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 667382972-Fluoro-4-iodo-5-(1-methoxymethoxy-ethyl)-pyridine

Product 1

HCID 667380961-(6-Fluoro-4-iodo-pyridin-3-yl)-ethanolYield 87.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 10340Sodium CarbonateSolvent

Procedure

Add 1 N HCl (5 mL) to a solution of 2-fluoro-4-iodo-5-(1-methoxymethoxy-ethyl)-pyridine (1 g, 3.2 mmol) in methanol (10 mL). Stir the mixture overnight. Dilute the reaction mixture with sodium carbonate (2 N). Extract the product into chloroform. Dry the organic phase over sodium sulfate. Concentrate the solution in vacuo. Purify the crude by column chromatography (10% methanol in DCM) to afford the title compound as a white solid (0.75 g, 87%). MS (ES) m/z 268 [M+1]+.

Workup

  1. extractionExtract the product into chloroform
  2. dry with materialDry the organic phase over sodium sulfate
  3. concentrationConcentrate the solution in vacuo
  4. customPurify the crude by column chromatography (10% methanol in DCM)

Sources & evidence

ORD record
ord-89b6f79c31fc4a85ba9a81ff89060754
Source dataset
uspto-grants-2012_02
Patent number
US08114872B2

Reaction notes

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