Hydrochloric Acid → 3-(4-Nitrophenyl)-3-oxopropanenitrile
Reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1)=[O:4].[C-:14]#[N:15].[Na+].Cl>C(O)C.O>[C:14]([CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1)=[O:4])#[N:15]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 2-bromo-4′-nitroacetophenone (30 g, 0.123 mol) in ethanol (200 mL) at 0° C. was added a solution of NaCN (18 g, 0.368 mol) in H2O (60 mL) dropwise over 1 h. Upon completion of the addition, the mixture was stirred at 0° C. for an additional hour and then diluted with H2O (200 mL). The solution was treated with 1N aq. HCl solution, to a pH of 2, and extracted with CH2Cl2 (2×500 ML). The combined organic layers were dried over Na2SO4 and concentrated by rotary evaporation. The residue was purified by flash chromatography on silica gel eluting with 1:1 hexane/EtOAc to obtain 2-cyano-4′nitroacetophenone as an orange solid.
Workup
- additionUpon completion of the addition
- extractionextracted with CH2Cl2 (2×500 ML)
- dry with materialThe combined organic layers were dried over Na2SO4
- concentrationconcentrated by rotary evaporation
- customThe residue was purified by flash chromatography on silica gel eluting with 1:1 hexane/EtOAc
Sources & evidence
- ORD record
- ord-e56148dc6f2d4fbf9891222ab662e938
- Source dataset
- uspto-grants-2003_03
- Patent number
- US06531478B2
Reaction notes
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