Ammonium Chloride → 4'-Chloro-3'-fluoroacetophenone

To a solution of 1-bromo-4-chloro-3-fluorobenzene (2.09 g, 10 mmol) in dry diethyl ether (12.0 ml) was added a solution of n-BuLi (1.55M in hexane, 6.77ml, 10.5 mmol) at −78° C. under nitrogen atmosphere. The mixture was allowed to warm to −20_C stirred for 45 min. A solution of N,N-dimethylacetamide (1.04 ml, 11.2 mmol) in diethyl ether (1.5 ml) was added and the mixture stirred for an additional 1 h. The mixture was then allowed to warm to room temperature. After stirring for 3 h, the reaction mixture was poured into saturated aqueous ammonium chloride (20 ml) and extracted with diethyl ether (30 ml×3). The combined organic layers were washed with 2N aqueous HCl (20 ml), saturated aqueous sodium bicarbonate (20 ml), brine (20 ml), and dried (MgSO4). Removal of solvent gave the title compound as a yellow oil (quant.).

1. temperatureto warm
2. stirringthe mixture stirred for an additional 1 h
3. stirringAfter stirring for 3 h
4. extractionextracted with diethyl ether (30 ml×3)
5. washThe combined organic layers were washed with 2N aqueous HCl (20 ml), saturated aqueous sodium bicarbonate (20 ml), brine (20 ml)
6. dry with materialdried (MgSO4)
7. customRemoval of solvent

ORD record

ord-11cf374f06704200965c8e42de6246eb

Source dataset

uspto-grants-2003_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06608070B1