Ethylene Glycol → 2-Bromo-4-[1,3]dioxolan-2-yl-5-fluoro-pyridine

HRID 1629738Notes

Reaction equation

HRID 1629738 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:7]([F:10])=[CH:8][N:9]=1)[CH:5]=[O:6].[CH2:11](O)[CH2:12][OH:13].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]2[O:13][CH2:12][CH2:11][O:6]2)[C:7]([F:10])=[CH:8][N:9]=1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 521998p-Toluenesulfonic acid monohydrateHCID 454803282-Bromo-5-fluoroisonicotinaldehyde

Product 1

HCID 575173372-Bromo-4-[1,3]dioxolan-2-yl-5-fluoro-pyridine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2-bromo-5-fluoroisonicotinaldehyde (495 mg, 2.43 mmol), ethylene glycol (0.27 mL, 4.85 mmol) and p-toluenesulfonic acid monohydrate (508 mg, 2.67 mmol) in toluene (13.5 mL) was refluxed for 4 hours. The mixture was concentrated and taken up in CH2Cl2, washed with 1 M NaOH, dried over sodium sulfate, filtered and concentrated. The crude product was purified by flash chromatography on silica gel (cyclohexane/EtOAc) to give INT 44.

Workup

  1. temperaturewas refluxed for 4 hours
  2. concentrationThe mixture was concentrated
  3. washwashed with 1 M NaOH
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by flash chromatography on silica gel (cyclohexane/EtOAc)
  8. customto give INT 44

Sources & evidence

ORD record
ord-4ab3fb1640904b24b1839d2713435a50
Source dataset
uspto-grants-2014_07
Patent number
US08791100B2

Reaction notes

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