1-(4-Bromo-2-fluorophenyl)propan-1-one

Synthesis

General procedure for the synthesis of 1-(4-bromo-2-fluorophenyl)propan-1-one from 1-(4-bromo-2-fluorophenyl)propan-1-ol: To a solution of 1-(4-bromo-2-fluorophenyl)propan-1-ol (5.8 g, 24.89 mmol) in DMF (30 ml) was added pyridinium dichromate (14.04 g, 37.33 mmol) at room temperature. After the reaction was carried out for 12 hours, the reaction mixture was quenched with water, diluted with ethyl acetate and filtered through diatomaceous earth. The organic layer was washed with brine solution, dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford the target product 1-(4-bromo-2-fluorophenyl)propan-1-one as a colorless liquid (4.4 g, 76% yield). The product was confirmed by 1H-NMR (DMSO-d6, 400MHz): δ7.78 (t, J=8.1Hz, 1H), 7.38 (m, 2H), 2.55 (m, 2H), 1.21 (t, J=7.1Hz, 3H).

References

[1] Journal of Medicinal Chemistry, 2017, vol. 60, # 9, p. 3703 - 3726
[2] Patent: US2011/118257, 2011, A1. Location in patent: Page/Page column 98
[3] Patent: EP2669270, 2013, A1. Location in patent: Paragraph 0816-0817
[4] Journal of Medicinal Chemistry, 2018,