Hydrochloric Acid → (4-Bromophenyl)(4-fluorophenyl)methanone

4-bromobenzoic acid (17-a, 10 g, 0.05 mol) was dissolved in SOCl2 (100 ml) and the resulting mixture was stirred at rt for 3 hours, then concentrated under vacuum. The residue was dissolved in 1-fluorobenzene (24 g, 0.25 mol) and AlCl3 (8.24 g, 0.06 mol) was added portion-wise with stirring under N2. The resulting reaction mixture was refluxed overnight. The reaction mixture was cooled to temperature and poured into 20% HCl (1500 ml), stirred for 1 h, and the layers were separated. The aqueous layer was further extracted with DCM (2×50 ml). The combined organic layer was washed with water, brine, dried (Na2SO4), filtered and concentrated under reduced pressure. The residue was washed with hexane to afford the product, 17-b, (12.2 g, 85%).

1. concentrationconcentrated under vacuum
2. stirringwith stirring under N2
3. customThe resulting reaction mixture
4. temperaturewas refluxed overnight
5. temperatureThe reaction mixture was cooled to temperature
6. stirringstirred for 1 h
7. customthe layers were separated
8. extractionThe aqueous layer was further extracted with DCM (2×50 ml)
9. washThe combined organic layer was washed with water, brine
10. dry with materialdried (Na2SO4)
11. filtrationfiltered
12. concentrationconcentrated under reduced pressure
13. washThe residue was washed with hexane

ORD record

ord-8e5fc4c44faa46ba838764019d856d6e

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09079930B2