Ethylene Glycol → 2-Bromo-5-(1,3-dioxolan-2-YL)pyridine

HRID 1186403Notes

Reaction equation

HRID 1186403 reaction equation
[Br:1]C1C(C=O)=CC=CN=1.[CH2:10]([OH:13])[CH2:11][OH:12].ClC1C=C(S(NC2[C:35](OCC3C=CC4C(=CC=CC=4)C=3)=[N:34][C:33]3C(=[CH:29][CH:30]=[CH:31][CH:32]=3)N=2)(=O)=O)C=C(Cl)C=1.O>C1(C)C=CC=CC=1>[Br:1][C:33]1[CH:32]=[CH:31][C:30]([CH:29]2[O:13][CH2:10][CH2:11][O:12]2)=[CH:35][N:34]=1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 962WaterHCID 47149512-BromonicotinaldehydeHCID 67402069HCID 67402069, compound

Product 1

HCID 184696682-Bromo-5-(1,3-dioxolan-2-YL)pyridineYield 992.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

6 Bromo-3-pyridinecarboxaldehyde (1.03 g, 5.54 mmol), ethylene glycol (370 μL, 6.65 mol) and Amberlyst 15 (200 mg) were suspended in toluene (100 mL). The mixture was heated to reflux under a nitrogen atmosphere for 12 hours, during which produced water was removed by use of a Dean-Stark trap. The reaction mixture was filtered and the mother liquid was concentrated. The residue was purified by column chromatography (hexane/ethyl acetate=7/3) to give 2-bromo-5-(1,3-dioxolan-2-yl)pyridine (895 mg, yield: 70%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux under a nitrogen atmosphere for 12 hours, during which
  3. customwas removed by use of a Dean-Stark trap
  4. filtrationThe reaction mixture was filtered
  5. concentrationthe mother liquid was concentrated
  6. customThe residue was purified by column chromatography (hexane/ethyl acetate=7/3)

Sources & evidence

ORD record
ord-ea49c234fd2f4479a98e5600fb3d1f61
Source dataset
uspto-grants-2014_03
Patent number
US08673908B2

Reaction notes

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