反应详情

To a solution of THF (800 mL) cooled in an ice-salt/water bath was added 3-fluoro-N-methoxy-N-methyl-4-nitrobenzamide followed by addition of 1 M DIBAL in THF by addition funnel over 30 min. The solution was allowed to stir under N2 for 1 h. The reaction mixture was then carefully diluted with 1N HCl (500 mL) and EtOAc (500 mL), transferred to separatory funnel, and separated. The organic phase was washed with 1N HCl (3×250 mL), 1N NaOH (2×250 mL), and water (250 mL). All aqueous layers were back extracted with EtOAc (2×250 mL). The organic layers were combined, dried (MgSO4), filtered, and concentrated in vacuo to afford 67 g of the above compound (396 mmol, yield 88%). 1H-NMR (DMSO-d6) 10.06 (s, 1H), 8.36 to 8.32 (t, J=7.8 Hz, 1H), 8.06 to 8.03 (d, J=11.2 Hz, 1H), 7.95 to 7.93 (d, J=9.1 Hz, 1H).

1. customtransferred to separatory funnel
2. customseparated
3. washThe organic phase was washed with 1N HCl (3×250 mL), 1N NaOH (2×250 mL), and water (250 mL)
4. extractionAll aqueous layers were back extracted with EtOAc (2×250 mL)
5. dry with materialdried (MgSO4)
6. filtrationfiltered
7. concentrationconcentrated in vacuo