Ethylene Glycol → 2-Bromo-6-(1,3-dioxolan-2-yl)pyridine

HRID 1432416Notes

Reaction equation

HRID 1432416 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([CH:8]=[O:9])[CH:5]=[CH:4][CH:3]=1.[CH2:10](O)[CH2:11][OH:12].CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]([CH:8]2[O:12][CH2:11][CH2:10][O:9]2)[N:7]=1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 27570096-Bromopyridine-2-carbaldehyde

Product 1

HCID 1186132-Bromo-6-(1,3-dioxolan-2-yl)pyridineYield 80%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 6-bromo-pyridine-2-carbaldehyde (2.0 g, 10.75 mmol), ethylene glycol (3 mL, 53.75 mmol), and a catalytic amount of TsOH in toluene (50 mL) was heated to reflux with a Dean-Stark trap for 1.5 hours and cooled down to room temperature and concentrated in vacuo. The residue was purified on silica gel column with 2% EtOAc in CH2Cl2 to yield 2-bromo-6-[1,3]dioxolan-2-yl-pyridine as a colorless liquid (1.97 g, 80%).

Workup

  1. temperatureto reflux with a Dean-Stark trap for 1.5 hours
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified on silica gel column with 2% EtOAc in CH2Cl2

Sources & evidence

ORD record
ord-0be31423da204ee7ba9786ea823e6043
Source dataset
uspto-grants-2009_11
Patent number
US07612094B2

Reaction notes

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