Butyryl chloride → 4'-Fluorobutyrophenone

Temperature

25 °C

Aluminum chloride (1.39 g, 1.04 mol) was added to a solution of butyryl chloride (55.45 g, 0.520 mol, Aldrich) in dichloromethane (500 ml) stirring under a nitrogen atmosphere at 25° C. A solution of fluorobenzene (50.1 g, 0.521 mol, Aldrich) in dichloromethane was added and stirring was continued for 18 h. The reaction solution was poured over ice and extracted with dichloromethane (3×400 ml). The combined dichloromethane extractions were washed with deionized water (2×250 ml), 1.0N hydrochloric acid (500 ml), saturated sodium bicarbonate solution (2×500 ml) and deionized water (4×250 ml), concentrated by spin evaporation in vacuo. This material was combined with material from a similar preparation (using 0.26 mol of fluorobenzene) for distillation. Distillation at reduced pressure gave 69.27 g (53%) of 4'-fluorobutyrophenone as a pale yellow liquid which later partially crystallized, b.p. 108-112° C. at 30 millitorr: NMR (DMSO-d6): d 8.03 (q, 2H, J=9.0 Hz and 5.6 Hz), 7.31 (t, 2H, J=8.9 Hz), 2.97 (t, 2H, J=7.0 Hz), 1.65-1.55 (m, 2H), 0.91 (t, 3H, J=7.3 Hz).

1. stirringstirring
2. additionThe reaction solution was poured over ice
3. extractionextracted with dichloromethane (3×400 ml)
4. extractionThe combined dichloromethane extractions
5. washwere washed with deionized water (2×250 ml), 1.0N hydrochloric acid (500 ml), saturated sodium bicarbonate solution (2×500 ml) and deionized water (4×250 ml)
6. concentrationconcentrated by spin evaporation in vacuo
7. distillationDistillation at reduced pressure

ORD record

ord-683ec53c43264f14bdb654ed5db40adf

Source dataset

uspto-grants-2000_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06124284