Water → 2-Fluoro-6-nitrobenzaldehyde

Temperature

140 °C

To a solution of 4-fluoro-2-nitrotoluene (3 g, 17.96 mmol) in DMF (25 ml) was added (MeO)2CHNMe2 (3.12 ml, 23.35 mmol) and the mixture warmed at 140° C. for 4 hours in argon atmosphere. Then the solution was allowed to reach room temperature and diethyl ether (100 ml) and water (100 ml) was added. The organic layer was washed with water (2×100 ml) and brine (1×100 ml), dried (MgSO4) and solvent concentrated at reduced pressure, affording an oil which was treated with NaIO4 (11.5 g, 53.6 mmol). The mixture was stirred in 50% aqueous THF (100 ml) at room temperature for 24 hours. The mixture was filtered in a celite pad and eluted with EtOAc. The organic layer was washed with NaHCO3 (saturated solution, 3×100 ml), dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash chromatography (50% CH2Cl2 /Hexane) affording 2-nitro-6-fluorobenzaldehyde as a brown solid.

1. customto reach room temperature
2. washThe organic layer was washed with water (2×100 ml) and brine (1×100 ml)
3. dry with materialdried (MgSO4) and solvent
4. concentrationconcentrated at reduced pressure
5. customaffording an oil which
6. filtrationThe mixture was filtered in a celite pad
7. washeluted with EtOAc
8. washThe organic layer was washed with NaHCO3 (saturated solution, 3×100 ml)
9. dry with materialdried over Na2SO4
10. concentrationconcentrated in vacuo
11. customThe residue was purified by flash chromatography (50% CH2Cl2 /Hexane)

ORD record

ord-c149d81fc02d45d287d562b2fee18e6c

Source dataset

uspto-grants-1999_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05929072