Quinoline → 3-Bromo-2-chloro-5-(trifluoromethyl)pyridine
Reaction equation
P(Cl)(Cl)([Cl:3])=O.N1C2C(=CC=CC=2)C=CC=1.[Br:16][C:17]1[C:18](O)=[N:19][CH:20]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:22]=1.C(=O)([O-])O.[Na+]>O>[Cl:3][C:18]1[C:17]([Br:16])=[CH:22][C:21]([C:23]([F:26])([F:25])[F:24])=[CH:20][N:19]=1Participants
6
Conditions
- Temperature
- 120 °C
Procedure
To phosphorous oxychloride (2.02 ml, 21.6 mmol) was added quinoline (1.34 ml, 11.2 mmol) followed by 3-bromo-2-hydroxy-5-trifluoromethylpyridine (5.0 g, 20.7 mmol), and the mixture formed heated at 120° C. for 3 hrs. It was then cooled to 100° C. and water (10 ml) added. After cooling to 22° C., sodium hydrogen carbonate solution (100 ml) was added and the mixture extracted with ethyl acetate (2×100 ml). The extracts were dried (MgSO4) and concentrated, and the residue purified by silica chromatography to give the product as an oil (4.05 g, 75% yield).
Workup
- customthe mixture formed
- temperatureIt was then cooled to 100° C.
- temperatureAfter cooling to 22° C.
- extractionthe mixture extracted with ethyl acetate (2×100 ml)
- dry with materialThe extracts were dried (MgSO4)
- concentrationconcentrated
- customthe residue purified by silica chromatography
Sources & evidence
- ORD record
- ord-bd7eab3c80da44cf87990a64417c9bb6
- Source dataset
- uspto-grants-2001_05
- Patent number
- US06225320B1
Reaction notes
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