Hydrogen Bromide → 4-Fluorophenylglyoxal hydrate

4-Fluoroacetophenone (27.6 g, 0.2 moles) was dissolved in dimethylsulfoxide (140 ml). 48% Hydrobromic acid (101.1 g, 68.0 ml, 0.6 moles) was added over 20 minutes. The resulting solution was aged at 55-60° C. for 22 hours. The mixture was cooled to room temperature and partitioned between water (1.0 liters) and ethyl acetate (250 ml). The aqueous phase was extracted with ethyl acetate (2×250 ml). The combined ethyl acetate extracts were filtered and solvent switched to toluene at 60° C. under reduced pressure. The solution was diluted to 200 ml with toluene, and water (10 ml) was added. The resulting slurry was stirred at room temperature for 18 hours then at 0° C. for 1 hour. The product was collected by filtration and washed with cold toluene (50 ml). The solid was sucked down on the filter for 30 minutes and air dried to constant weight to afford 4-fluorophenylglyoxal hydrate (24.8 g) as a white solid in 73% yield.

1. custompartitioned between water (1.0 liters) and ethyl acetate (250 ml)
2. extractionThe aqueous phase was extracted with ethyl acetate (2×250 ml)
3. filtrationThe combined ethyl acetate extracts were filtered
4. customswitched to toluene at 60° C. under reduced pressure
5. additionThe solution was diluted to 200 ml with toluene, and water (10 ml)
6. additionwas added
7. waitat 0° C. for 1 hour
8. filtrationThe product was collected by filtration
9. washwashed with cold toluene (50 ml)
10. filtrationfilter for 30 minutes
11. customair dried to constant weight

ORD record

ord-72273756a42c4f77a9cf7530c993b8a1

Source dataset

uspto-grants-2000_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06046325