Dimethylformamide → 2-Fluoro-4,6-dimethoxybenzaldehyde
Reaction equation
[F:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([O:10][CH3:11])[CH:3]=1.P(Cl)(Cl)(Cl)=O.CN([CH:20]=[O:21])C>>[F:1][C:2]1[CH:3]=[C:4]([O:10][CH3:11])[CH:5]=[C:6]([O:8][CH3:9])[C:7]=1[CH:20]=[O:21]Participants
4
Procedure
To a solution of 1-fluoro-3,5-dimethoxybenzene (3.12 g, 20.0 mmol) in DMF (15 mL) was added dropwise phosphoryl trichloride (1.55 mL) at 0° C. The reaction mixture was stirred at room temperature overnight and poured onto ice. The resulting mixture was extracted with ethyl acetate (2×50 mL) and the combined organic layers were dried over anhydrous Na2SO4, concentrated in vacuo. The residue was purified by column chromatography on silica gel (EtOAc/PE=1/8) to give the title compound as a yellow solid (2.75 g, Yield: 74.6%). 1H NMR (400 MHz, DMSO-d) δ 10.15 (s, 1H), 6.52-6.56 (m, 2H), 3.91 (s, 3H), 3.88 (s, 3H). MS (ESI) m/z=185 [M+H]+.
Workup
- additionpoured onto ice
- extractionThe resulting mixture was extracted with ethyl acetate (2×50 mL)
- dry with materialthe combined organic layers were dried over anhydrous Na2SO4
- concentrationconcentrated in vacuo
- customThe residue was purified by column chromatography on silica gel (EtOAc/PE=1/8)
Sources & evidence
- ORD record
- ord-1cf9a8222b25454e919aae442739491f
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08343944B2
Reaction notes
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