Fluorobenzene → 2-Chloro-1-(4-fluorophenyl)propan-1-one

A solution of 2-chloropropionyl chloride (49 ml) in dichloromethane (50 ml) was added to a mixture of anhydrous aluminium trichloride (55.5 g) in dichloromethane (120 ml). The mixture was stirred for 10 minutes at room temperature and then a solution of fluorobenzene (39.5 ml) in dichloromethane (30 ml) was added dropwise. The resulting mixture was stirred for one hour, allowed to stand for 16 hours and then poured on to an icehydrochloric acid mixture. The two phase mixture was vigorously stirred at room temperature for 11/2 hours, separated and the aqueous layer washed with dichloromethane (2×50 ml). The combined organic extracts were then washed with aqueous sodium hydroxide (3N, 2×100 ml), water (1×100 ml) and brine (1×100 ml), dried (MgSO4) and evaporated under reduced pressure to afford 2-chloro-1-(4-fluorophenyl)-1-propanone, 71.3 g.

1. stirringThe resulting mixture was stirred for one hour
2. waitto stand for 16 hours
3. additionpoured on to an icehydrochloric acid mixture
4. stirringThe two phase mixture was vigorously stirred at room temperature for 11/2 hours
5. customseparated
6. washthe aqueous layer washed with dichloromethane (2×50 ml)
7. washThe combined organic extracts were then washed with aqueous sodium hydroxide (3N, 2×100 ml), water (1×100 ml) and brine (1×100 ml)
8. dry with materialdried (MgSO4)
9. customevaporated under reduced pressure

ORD record

ord-aa440719dc4e4fc48cbdbdb6c72bf8a7

Source dataset

uspto-grants-1991_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05066653