1-bromo-4-phenylbutan-2-one

Synthesis Reference(s)

The Journal of Organic Chemistry, 50, p. 5140, 1985 DOI: 10.1021/jo00225a032

Synthesis

General procedure for the synthesis of 1-bromo-4-phenylbutan-2-one from benzylacetone: Bromine (19 mL, 1.1 mmol) was slowly added to a stirred solution of 4-phenylbutan-2-one (50 g, 1 mmol) in methanol (350 mL) at 0 °C. The reaction mixture was stirred continuously at 15°C for 4 hours. Upon completion of the reaction, the reaction mixture was diluted with water (500 mL) and extracted with dichloromethane (2 x 500 mL). The organic layers were combined, washed with brine solution, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was dissolved in petroleum ether and crystallized in a refrigerator for 5 hours. The solid was collected by filtration to afford the target product 1-bromo-4-phenylbutan-2-one (72 g, 93.98%) as a white solid.1H NMR (300 MHz, CDCl3): δ 2.9 (q, 4H), 3.8 (s, 2H), 7.2 (m, 3H), 7.3 (m, 2H).13C NMR (100 MHz, CDCl3): δ 29.87,34.24,41.38,126.34 (2c), 128.28 (2c), 128.57,140.29,201.18.

References

[1] Journal of Chemical Sciences, 2015, vol. 127, # 11, p. 2023 - 2028
[2] Patent: KR2017/25682, 2017, A. Location in patent: Paragraph 0093; 0094-0097
[3] Patent: US2003/149294, 2003, A1
[4] Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 9, p. 3225 - 3234
[5] Synthetic Communications, 2012, vol. 42, # 9, p. 1288 - 1305