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

HRID 931086Notes

Reaction equation

HRID 931086 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]>C1(C)C=CC=CC=1.C(OCC)(=O)C.C1(C)C=CC(S(O)(=O)=O)=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

6

Reactant 2

HCID 174Ethylene GlycolHCID 27570096-Bromopyridine-2-carbaldehyde

Product 1

HCID 1186132-Bromo-6-(1,3-dioxolan-2-yl)pyridineYield 99.2%

Reagents, catalysts & solvents 3

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 6-bromopyridine-2-carbaldehyde (3 g, 16.22 mmol) in toluene (60 mL) was added ethylene glycol (4.97 g, 80.2 mmol) and p-toluenesulphonic acid (0.152 g, 0.8 mmol). The reaction mixture was refluxed for 3 h. The solvent was removed under reduced pressure to afford the crude which was dissolved in ethyl acetate and washed with water. The organic layers were washed with a brine solution, and dried over sodium sulfate. The solvent was removed under reduced pressure to afford 2-bromo-6-(1,3-dioxolan-2-yl)pyridine (3.7 g). The material was used for the next step without further purification.

Workup

  1. temperatureThe reaction mixture was refluxed for 3 h
  2. customThe solvent was removed under reduced pressure
  3. customto afford the crude which
  4. washwashed with water
  5. washThe organic layers were washed with a brine solution
  6. dry with materialdried over sodium sulfate
  7. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-45a1a7a62fd74303b1573ae4219afdec
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

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