Isopropyl Acetate → 5-Bromo-3-nitropyridine-2-carbonitrile
Reaction equation
Br[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([Br:11])=[CH:4][N:3]=1.[Cu](C#N)[C:13]#[N:14].C(OC(C)C)(=O)C>C(#N)CC.[Cl-].[Na+].O>[Br:11][C:5]1[CH:6]=[C:7]([N+:8]([O-:10])=[O:9])[C:2]([C:13]#[N:14])=[N:3][CH:4]=1Participants
6
Conditions
- Temperature
- 90 °C
Procedure
The compound of Step 1 (1 eq) was suspended in propionitrile (3 vol). Copper cyanide (1.1 eq) was added and the mixture was heated to 90° C. and aged for about 17 h. The reaction mixture was cooled to room temperature and isopropyl acetate (12 vol) and saturated brine (8 vol) were added. The mixture was stirred for 15 min and the layers were cut. The top organic layer was washed with brine (4×6 vol). The batch concentrated under reduced pressure to yield the desired product.
Workup
- temperatureThe reaction mixture was cooled to room temperature
- washThe top organic layer was washed with brine (4×6 vol)
- concentrationThe batch concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-f708e91714e94f44879617a21c4a94a2
- Source dataset
- uspto-grants-2010_09
- Patent number
- US07790754B2
Reaction notes
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