Citric Acid → 3-Bromopyridine-2-carbaldehyde
Reaction equation
[Br:1][C:2]1[C:3]([CH:8](Br)Br)=[N:4][CH:5]=[CH:6][CH:7]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)[OH:14]>N1CCOCC1.CCOC(C)=O>[Br:1][C:2]1[C:3]([CH:8]=[O:14])=[N:4][CH:5]=[CH:6][CH:7]=1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 60 °C
Procedure
A suspension of 3-bromo-2-dibromomethyl-pyridine (10.0 g, 30.32 mmol) in morpholine (30.0 mL) was heated at 60° C. for 1 h. The reaction mixture was then cooled to rt and diluted with EtOAc (200 mL) followed by adjustment to pH 4 by adding citric acid (40.0 g). The reaction mixture was extracted with EtOAc (3×200 mL). The combined organic layers were dried over Na2SO4 and concentrated under reduced pressure. The resulting residue was purified by column chromatography using silica (100-200 mesh) and 3% EtOAc in hexane as eluent to give 3-bromo-pyridine-2-carbaldehyde. 1H-NMR (400 MHz, CDCl3) δ ppm 10.23 (s, 1H), 8.75 (d, 1H), 8.03 (d, 1H), 7.32 (t, 1H).
Workup
- temperatureThe reaction mixture was then cooled to rt
- extractionThe reaction mixture was extracted with EtOAc (3×200 mL)
- dry with materialThe combined organic layers were dried over Na2SO4
- concentrationconcentrated under reduced pressure
- customThe resulting residue was purified by column chromatography
Sources & evidence
- ORD record
- ord-b7e36e7bd7e14790ad776dd7d16178dd
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08778941B2
Reaction notes
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