1-Bromo-3-fluorobenzene → 1-(4-Bromo-2-fluorophenyl)propan-1-one

Temperature

90 °C

A mixture of 3-fluorobromobenzene (5.0 g, 29 mmol) and aluminium (III) chloride (11.6 g, 87 mmol) was heated under argon until a slurry formed. Propionyl chloride (3.2 g, 35 mmol) was added over 15 min and the mixture was heated at 90° C. for 1 h. The reaction was poured onto ice-water (100 mL) and the resultant mixture was extracted with dichloromethane (3×50 mL). The combined organic extracts were dried (magnesium sulfate), concentrated in vacuo and purified by column chromatography (SiO2; heptane) to give the product (1.2 g, 18%) as a colourless oil: NMR δH (400 MHz, CDCl3) 1.18 (3H, t, J 7.5), 2.95 (2H, m), 7.29-7.38 (2H, m) and 7.75 (1H, t, J 8 Hz).

1. temperaturewas heated under argon until a slurry
2. customformed
3. additionThe reaction was poured onto ice-water (100 mL)
4. extractionthe resultant mixture was extracted with dichloromethane (3×50 mL)
5. dry with materialThe combined organic extracts were dried (magnesium sulfate)
6. concentrationconcentrated in vacuo
7. custompurified by column chromatography (SiO2; heptane)

ORD record

ord-8594186240304822884a7cc6d76846d5

Source dataset

uspto-grants-2003_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06552062B1