N-(4-Bromo-3-fluoro-2-methylphenyl)acetamide → N-(4-Cyano-3-fluoro-2-methylphenyl)acetamide
Reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:11])[CH3:10])=[C:4]([CH3:12])[C:3]=1[F:13].[C:14]([Cu])#[N:15]>CN(C=O)C>[C:14]([C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:11])[CH3:10])=[C:4]([CH3:12])[C:3]=1[F:13])#[N:15]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 150 °C
Procedure
To a solution of N-(4-bromo-3-fluoro-2-methylphenyl)acetamide (72B) (2.18 g, 8.86 mmol) in DMF (20 mL) was added CuCN (2.61 g, 29.1 mmol). The mixture was stirred at 150° C. for 12 h and was then poured into ice (50 g). After warming to rt, the product was extracted with EtOAc (3×50 mL). The combined organic layers were washed with brine, dried and concentrated. The residue was purified via flash chromatography eluting with a solution of 5% methanol in 95% of EtOAc/hexane (1:1) to provide the title compound (1.51 g) as a white solid. LCMS: m/z 193 [M+H]+
Workup
- temperatureAfter warming to rt
- extractionthe product was extracted with EtOAc (3×50 mL)
- washThe combined organic layers were washed with brine
- customdried
- concentrationconcentrated
- customThe residue was purified via flash chromatography
- washeluting with a solution of 5% methanol in 95% of EtOAc/hexane (1:1)
Sources & evidence
- ORD record
- ord-8080fcf545a8485b8dbff7794af3c7b6
- Source dataset
- uspto-grants-2008_07
- Patent number
- US07405234B2
Reaction notes
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