Water → a-Acetyl-2,6-difluoro-4-methoxybenzeneacetonitrile
Reaction equation
[O-:1][CH2:2][CH3:3].[Na+].[F:5][C:6]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[C:8]([F:14])[C:7]=1[CH2:15][C:16]#[N:17].O>C1(C)C(C)=CC=CC=1.C(O)C.C(OCC)(=O)C>[C:2]([CH:15]([C:7]1[C:8]([F:14])=[CH:9][C:10]([O:12][CH3:13])=[CH:11][C:6]=1[F:5])[C:16]#[N:17])(=[O:1])[CH3:3]Participants
7
Conditions
- Temperature
- 50 °C
Procedure
Solid sodium ethoxide (4.7 g, 66 mmol) was stirred in a mixture of xylene (20 mL) and ethanol (10 mL) and heated to 50° C. A solution of 2,6-difluoro-4-methoxybenzeneacetonitrile (i.e. the product of Step A) (8.0 g, 44 mmol) in ethyl acetate (10.4 mL) was added dropwise. The reaction mixture was heated at 50° C. for 4 h and then allowed to cool to ambient temperature. The reaction mixture was poured into water (100 mL) and extracted with ethyl acetate (25 mL). The aqueous phase was acidified with 3 N aqueous HCl to pH 4 and extracted with ethyl acetate (100 mL). This organic phase was washed with water (50 mL), brine (50 mL), then dried over MgSO4, and concentrated to leave the title compound as a tan semisolid (8.0 g).
Workup
- temperatureThe reaction mixture was heated at 50° C. for 4 h
- temperatureto cool to ambient temperature
- extractionextracted with ethyl acetate (25 mL)
- extractionextracted with ethyl acetate (100 mL)
- washThis organic phase was washed with water (50 mL), brine (50 mL)
- dry with materialdried over MgSO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-8544af4176374a5ba15fc14c9dea8ed6
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09107412B2
Reaction notes
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