Ethanol → 3,5-Dibromo-1,2-benzenediamine

3,5-Dibromo-1,2-diaminobenzene was prepared using an adaptation of the method of Bellamy, et al. (Bellamy, F. D. et al., Tetrahedron Lett. 25:839 (1984)). A mixture of 2,4-dibromo-6-nitroaniline (500 mg, 1.69 mmol) and SnCl2 ·2H2O (1.90 g, 8.45 mmol) dissolved in 5 mL ethyl acetate and 2 mL absolute ethanol under N2 was heated at 70° C. for 1 h. All the starting material had reacted as evidenced by TLC (silica gel, 3:1 hexanes:ethyl acetate). The reaction was allowed to cool to room temperature and poured into 20 mL crushed ice. Sufficient sat'd NaHCO3 solution was added (foaming ) to bring the pH to 5. The thick yellow white emulsion was vacuum filtered and the filtrate extracted with 3×25 mL ethyl acetate and the combined organic extracts washed with sat'd NaCl solution. The organic phase was dried (MgSO4), vacuum filtered and the solvent rotary evaporated to yield a pale yellow oil which crystallized on standing to yield 400 mg (89%). 1H NMR (CDCl3) δ3.62 (br s, 4H, 2(NH2)); 6.78 (d, J=1.8, 1H, H-6); 7.01 (d, J=1.8, 1H, H-4).

1. customAll the starting material had reacted
2. additionpoured into 20 mL
3. customcrushed ice
4. additionwas added (foaming )
5. filtrationfiltered
6. extractionthe filtrate extracted with 3×25 mL ethyl acetate
7. washthe combined organic extracts washed with sat'd NaCl solution
8. dry with materialThe organic phase was dried (MgSO4), vacuum
9. filtrationfiltered
10. customthe solvent rotary evaporated
11. customto yield a pale yellow oil which
12. customcrystallized
13. customto yield 400 mg (89%)

ORD record

ord-4473a23923b0435284005ab26e82f964

Source dataset

uspto-grants-1996_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05514680