p-Toluenesulfonic acid → 3-Bromo-4-(dimethoxymethyl)pyridine
Reaction equation
[C:1]1(C)C=CC(S(O)(=O)=O)=CC=1.[Br:12][C:13]1[CH:20]=[N:19][CH:18]=[CH:17][C:14]=1[CH:15]=[O:16].[C:21](OCC)(=[O:23])C>CO.CCCCCC>[Br:12][C:13]1[CH:20]=[N:19][CH:18]=[CH:17][C:14]=1[CH:15]([O:23][CH3:21])[O:16][CH3:1]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 75 °C
Procedure
p-Toluene sulphonic acid (PTSA) (613.5 mg, 3.225 mmol) was added to a stirred solution of 3-bromoisonicotinaldehyde (500 mg, 2.688 mmol) in methanol (20 mL) and the resulting reaction mixture was stirred for 3 hours at 75° C. The reaction was monitored by TLC (10% ethyl acetate in hexane). The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The crude residue was diluted with ice, basified using saturated NaHCO3 solution and extracted using ethyl acetate. The organic layer was washed with water, brine solution, dried over Na2SO4 and concentrated under reduced pressure. Purification by column chromatography on silica gel (10% ethyl acetate in hexane) afforded 600 mg of the product (96.3% yield).
Workup
- customthe resulting reaction mixture
- temperatureThe reaction mixture was cooled to room temperature
- concentrationconcentrated under reduced pressure
- additionThe crude residue was diluted with ice
- extractionextracted
- washThe organic layer was washed with water, brine solution
- dry with materialdried over Na2SO4
- concentrationconcentrated under reduced pressure
- customPurification by column chromatography on silica gel (10% ethyl acetate in hexane)
Sources & evidence
- ORD record
- ord-94b7ec8671794e2c90f43b79de571854
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08946260B2
Reaction notes
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