627463-25-6

The general procedure for the synthesis of 4-bromo-2-ethyl-1-fluorobenzene (9ci) from 4-bromo-2-vinyl-1-fluorobenzene was as follows: the yellow oily substance (2.8 g, 10 mmol) obtained in step A was dissolved in ethyl acetate (200 mL). 10% palladium-carbon catalyst (250 mg) was added to the solution and the hydrogenation reaction was carried out at atmospheric pressure (1 atm) until thin layer chromatography (TLC) monitoring showed that the reaction was complete. Upon completion of the reaction, the catalyst was removed by filtration and the filtrate was concentrated to afford the target product 4-bromo-2-ethyl-1-fluorobenzene (9ci) as an oil in a yield of 2.4 g in 87%.

[1] Patent: US2004/6058, 2004, A1. Location in patent: Page/Page column 30
[2] Patent: WO2017/158151, 2017, A1. Location in patent: Page/Page column 101
[3] Patent: US2010/227894, 2010, A1. Location in patent: Page/Page column 74