Synthesis
The general procedure for the synthesis of 2,3-bis(bromomethyl)quinoxaline from o-phenylenediamine and 1,4-dibromo-2,3-butanedione was as follows: 6.52 g (27 mmol) of 1,4-dibromo-2,3-butanedione and 300 mL of ethanol were added to a 1,000 mL three-neck flask. Subsequently, a solution made from 2.94 g (27 mmol) of o-phenylenediamine dissolved in 150 mL of ethanol was added to the mixture with continuous stirring for 30 minutes at room temperature. White solid precipitation was observed during the reaction. To the reaction mixture, 200 mL of water was added and the white solid was collected by filtration and dried under reduced pressure to give 6.74 g (yield: 81%) of the target product 2,3-bis(bromomethyl)quinoxaline. The 1H nuclear magnetic resonance (1H-NMR) spectral data of the compound were as follows: 1H-NMR (CDCl3): δ 4.93 (s, 4H), 7.81 (q, 2H), 8.08 (q, 2H).
References
[1] Tetrahedron, 2013, vol. 69, # 4, p. 1403 - 1416
[2] Journal of Organic Chemistry, 2005, vol. 70, # 13, p. 5055 - 5061
[3] Organometallics, 2013, vol. 32, # 12, p. 3493 - 3501
[4] Synthetic Communications, 2011, vol. 41, # 3, p. 417 - 425
[5] Journal of Chemical Crystallography, 2006, vol. 36, # 3, p. 211 - 215
