2-Bromo-3-(2-methoxyvinyl)pyridine → 2-(2-Bromopyridin-3-yl)acetaldehyde
Reaction equation
[Br:1][C:2]1[C:7]([CH:8]=[CH:9][O:10]C)=[CH:6][CH:5]=[CH:4][N:3]=1>C(O)=O>[Br:1][C:2]1[C:7]([CH2:8][CH:9]=[O:10])=[CH:6][CH:5]=[CH:4][N:3]=1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
A solution of E and Z mixture of 2-bromo-3-(2-methoxyvinyl)pyridine (1.88 g, 8.79 mmol) in formic acid (96%, 10 mL) was stirred at 60° C. for 16 hours and at 80° C. for 3 hours before cooled to room temperature. Most of formic acid was removed. The mixture was diluted with ethyl acetate, washed with sodium bicarbonate and brine, dried over magnesium sulfate and concentrated. Purification by chromatography on silica gel gave 2-(2-bromopyridin-3-yl)acetaldehyde (864 mg, 53% yield) as yellow solid.
Workup
- temperaturebefore cooled to room temperature
- customMost of formic acid was removed
- additionThe mixture was diluted with ethyl acetate
- washwashed with sodium bicarbonate and brine
- dry with materialdried over magnesium sulfate
- concentrationconcentrated
- customPurification by chromatography on silica gel
Sources & evidence
- ORD record
- ord-ea9c824409cd4118858d85e339a173ce
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08362022B2
Reaction notes
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