2-Bromo-1-(4-dimethylamino-phenyl)-ethanone

Uses

2-Bromo-1-(4-dimethylaminophenyl)ethanone can be used as potential biomarkers for respiratory illness.

Synthesis

The general procedure for the synthesis of 2-bromo-1-(4-(dimethylamino)phenyl)ethanone from the compound (CAS: 210832-81-8) was as follows: 5.1 g (1 eq.) of the raw material was dissolved in 30 mL of THF, and cooled to 0°C. Subsequently, a mixed solution consisting of diethyl phosphite (2.04 mL, 1 eq.) and triethylamine (2.4 mL, 1.1 eq.) in 12 mL of THF was added slowly and dropwise. The reaction mixture was stirred at room temperature for 6 hours. Upon completion of the reaction, the solvent was removed by rotary evaporation and the residue was poured into 200 mL of ice water. The resulting precipitate was collected by filtration, washed with water and dried under vacuum to give the green solid product 3 in 89% yield. The structure of the product was confirmed by nuclear magnetic resonance hydrogen (1H NMR, CDCl3) and carbon (13C NMR, CDCl3) spectra: 1H NMR (CDCl3) δ 2.97 (s, 6H, 2×CH3), 4.45 (s, 2H, CH2), 6.57 (d, 2H, J = 9.0 Hz, 2×CHAr), 7.72 (d, 2H, CHAr); 13C NMR (CDCl3) δ 31.3 (1C, CH2), 40.4 (2C, CH3), 111.1 (2C, CHAr), 121.8 (1C, Cq), 131.6 (2C, CHAr), 154.1 (1C, Cq), 189.7 (1C, Cq).

References

[1] Tetrahedron Letters, 1998, vol. 39, # 28, p. 4987 - 4990
[2] Patent: US2007/258887, 2007, A1. Location in patent: Page/Page column 28; 39-40
[3] Chemical Communications, 2016, vol. 52, # 90, p. 13277 - 13280
[4] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 10, p. 2966 - 2968
[5] ACS Medicinal Chemistry Letters, 2013, vol. 4, # 7, p. 596 - 600