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

HRID 2246381Notes

Reaction equation

HRID 2246381 reaction equation
[Br:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]=[O:9])=[CH:4][CH:3]=1.[CH2:10](O)[CH2:11][OH:12]>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[O:12][CH2:11][CH2:10][O:9]2)=[CH:6][N:7]=1

Participants

4

Reactant 2

HCID 174Ethylene GlycolHCID 117692346-Bromo-3-pyridinecarboxaldehyde

Product 1

HCID 184696682-Bromo-5-(1,3-dioxolan-2-YL)pyridine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

6-Bromo-3-pyridinecarbaldehyde (500 mg, 2.7 mmol) and 1,2-ethanediol (200 mg, 3.2 mmol) are dissolved in toluene (50 ml) together with Amberlyst 15 (100 mg) in a round bottom flask equipped with a reflux condenser and a Dean-Stark trap. The solution is stirred at reflux overnight, then cooled to room temperature, filtered and concentrated in vacuo. The crude product is chromatographed over silica gel with cyclohexane and ethyl acetate as the eluent to afford the title compound as a colorless oil.

Workup

  1. customequipped with a reflux condenser
  2. temperatureat reflux overnight
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude product is chromatographed over silica gel with cyclohexane and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-f79083b1d10243a19898d27cc2c3e949
Source dataset
uspto-grants-2010_03
Patent number
US07687510B2

Reaction notes

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