51229-51-7

1-(4-(Bromomethyl)phenyl)ethanone is useful in the synthesis of series of dihydropyrimidine and thiopyrimidine derivatives as antiviral agents.

General procedure for the synthesis of 1-(4-(bromomethyl)phenyl)ethanone from 4'-methylacetophenone: To a solution of 1-(4-methylphenyl)ethanone (600 mg, 4.47 mmol) in carbon tetrachloride (15 mL) was added sequentially N-bromosuccinimide (955 mg, 5.37 mmol) and benzoyl peroxide (31 mg, 0.13 mmol). The reaction mixture was heated to reflux for 3 hours, then cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure to afford the target product 1-(4-(bromomethyl)phenyl)ethanone (683 mg, 71% yield) as a brown oil.LC-MS analysis showed the molecular ion peak [M+H]+ as 213.

[1] Journal of the American Chemical Society, 2006, vol. 128, # 5, p. 1404 - 1405
[2] Patent: CN103787966, 2016, B. Location in patent: Paragraph 0115-0117
[3] Journal of Medicinal Chemistry, 2017, vol. 60, # 18, p. 7703 - 7724
[4] Molecules, 2018, vol. 23, # 8, p. 1DUMMY
[5] Patent: CN107098791, 2017, A. Location in patent: Paragraph 0058-0060