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

HRID 561013Notes

Reaction equation

HRID 561013 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.C(Cl)(Cl)Cl>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

6

Reactant 3

HCID 313Hydrochloric AcidHCID 6212ChloroformHCID 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 2 N sodium carbonate. Abstract the product into chloroform. Dry the organic phase over sodium sulfate. Concentrate the solution in vacuo to a give the crude. Purify the crude by column chromatography (10% methanol in dichloromethane) to afford the product as a white solid (0.75 g, 87%). MS (ES) m/z 268 [M+1]+.

Workup

  1. dry with materialDry the organic phase over sodium sulfate
  2. concentrationConcentrate the solution in vacuo to
  3. customa give the crude
  4. customPurify the crude by column chromatography (10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-c70d1632d42c4832a40a2b798d5eaf5e
Source dataset
uspto-grants-2011_11
Patent number
US08063212B2

Reaction notes

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