Hydrochloric Acid → 259248-36-7
Reaction equation
C[O-].[Na+].C1(C)C=CC=CC=1.[F:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH2:18][C:19]#[N:20].Cl.[C:22](=O)([O:25]C)[O:23][CH3:24]>O>[C:19]([CH:18]([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[F:11])[C:22]([O:23][CH3:24])=[O:25])#[N:20]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 75 °C
Procedure
Sodium methoxide (51.84 g) was added to dry toluene (815 mL) in a 1 L reactor under a nitrogen atmosphere. The reaction mixture was heated to 75° C., and then a mixture of 2-fluorobenzeneacetonitrile (100 g) in dimethyl carbonate (131.64 g) was added at 70-74° C. over a period of 45 minutes. The reaction mixture was further maintained at this temperature (70-75° C.) for an additional 4.5 hours. The reaction mixture was then cooled to 25-30° C. and added to a mixture of HCl (110 g, 35.2 wt %) diluted with water (300 mL) at 10-15° C. using an addition funnel. The resulting layers were separated, and the aqueous layer was extracted with ethyl acetate (2×200 mL). The combined organic layers were washed with water (2×200 mL), dried over sodium sulfate, and concentrated under reduced pressure to provide the title compound as a brown oily liquid (138.8 g, 94.8% yield).
Workup
- additionwas added at 70-74° C. over a period of 45 minutes
- temperatureThe reaction mixture was further maintained at this temperature (70-75° C.) for an additional 4.5 hours
- temperatureThe reaction mixture was then cooled to 25-30° C.
- customThe resulting layers were separated
- extractionthe aqueous layer was extracted with ethyl acetate (2×200 mL)
- washThe combined organic layers were washed with water (2×200 mL)
- dry with materialdried over sodium sulfate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-ae29e418c5d441e1872f401691d7ecd2
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09210932B2
Reaction notes
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