Hydrochloric Acid → 6-Fluoro-4-iodopyridin-3-ol

HRID 561003Notes

Reaction equation

Cl.[F:2][C:3]1[CH:8]=[C:7]([I:9])[C:6]([O:10]COC)=[CH:5][N:4]=1.C(=O)(O)[O-].[Na+]>C1COCC1>[F:2][C:3]1[N:4]=[CH:5][C:6]([OH:10])=[C:7]([I:9])[CH:8]=1

Participants

Conditions

Temperature: 60 °C

Procedure

Add HCl (3 M in water, 31 mL, 93.01 mmol) to a solution of 2-fluoro-4-iodo-5-methoxymethoxy-pyridine (3.9 g, 13.78 mmol) in THF (20 mL). Stir the mixture at 60° C. for 3 hours. Cool down the mixture. Adjust the pH to 7 with slow addition of saturated aqueous sodium bicarbonate solution. Extract the solution with ethyl acetate three times. Wash the organic layer with saturated aqueous sodium chloride. Dry the mixture over sodium sulfate. Concentrate the solution in vacuo to afford the title compound (3.2 g, 97.18%) as a yellow solid. MS (EI) m/z 240 [M+1]+.

Workup

temperatureCool down the mixture
extractionExtract the solution with ethyl acetate three times
washWash the organic layer with saturated aqueous sodium chloride
dry with materialDry the mixture over sodium sulfate
concentrationConcentrate the solution in vacuo

Sources & evidence

ORD record: ord-e6a154c882884f59a91a136e5536f1dd
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08063212B2

Reaction notes

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