Hydrochloric Acid → 1261859-54-4

To a stirred solution of 4-bromo-3-chlorobenzoyl chloride (11 g, CAS 21900-32-3) in acetonitrile (50 ml) and THF (50 ml) at 0-5° C. was added dropwise (trimethylsilyl)diazomethane (26.0 ml, 2 M solution in diethyl ether). The reaction mixture was stirred at room temperature for 30 min. TLC analysis showed the reaction was complete. Hydrochloric acid (7.22 ml, 37% aq.) was then added dropwise at 0-5° C. over 10 minutes and the reaction mixture was then stirred at room temperature for a further 20 minutes. The reaction mixture was poured into EtOAc and extracted sequentially with aq. Na2CO3 solution, water and saturated brine. The organic layer was then dried over Na2SO4 and concentrated in vacuo to afford 1-(4-bromo-3-chlorophenyl)-2-chloroethanone (11.0 g, 95%) as a light brown solid which was used in the next step without further purification. MS (EI): 221 ([{81Br37Cl}M-CH2Cl]+), 219 ([{79Br37Cl/81Br35Cl}M-CH2Cl]+), 217 ([{79Br35Cl}M-CH2Cl]+), 193 ([{81Br37Cl}M-CH2Cl—CO]+), 191 ([{79Br37Cl/81Br35Cl}M-CH2Cl—CO]+), 189 ([{79Br35Cl}M-CH2Cl—CO]+).

1. stirringthe reaction mixture was then stirred at room temperature for a further 20 minutes
2. extractionextracted sequentially with aq. Na2CO3 solution, water and saturated brine
3. dry with materialThe organic layer was then dried over Na2SO4
4. concentrationconcentrated in vacuo

ORD record

ord-aaa0c5604b58443dafb5677fe4532923

Source dataset

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09029370B2