反应详情

A solution of 1-(2-chloroethoxy)-2,6-dibromo-4-fluoro-3-nitrobenzene (73.2 g, 0.19 mol) in ethanol (1.1 L) containing 7.3 g of 10% palladium on carbon was hydrogenated at 40 psi for 5 days. The catalyst was filtered and the solvent was removed. The residue was dissolved in diethyl ether (300 mL) and washed with saturated aqueous sodium carbonate (200 L). The organic layer separated and washed with water, dried over anhydrous magnesium sulfate, filtered, and the solvent removed to afford an oil which solidies to afford 32.5 g (90.0%) a dark solid: mp 42°-43° C.; MS EI m/e 189/191 (M+); 1H NMR (CDCl3) δ 3.40-3.60 (2H, bs, NH2), 3.77 (2H, d, J=6 Hz), 4.14 (2H, d, J=6 Hz), 6.19-6.23 (1H, m), 6.36 (1H, dd, J=7, 3 Hz), 6.88 (1H, dd, J=11, 9 Hz).

1. filtrationThe catalyst was filtered
2. customthe solvent was removed
3. dissolutionThe residue was dissolved in diethyl ether (300 mL)
4. washwashed with saturated aqueous sodium carbonate (200 L)
5. customThe organic layer separated
6. washwashed with water
7. dry with materialdried over anhydrous magnesium sulfate
8. filtrationfiltered
9. customthe solvent removed
10. customto afford an oil which