Water → 2-Bromo-1-(2,4,6-trichlorophenyl)ethanone

Temperature

80 °C

A mixture of 1,3,5-trichlorobenzene (10.0 g, 55.1 mmol), 2-bromoacetyl bromide (5.0 mL, 57.8 mmol, 1.05 eq), and aluminum chloride (7.7 g, 57.8 mmol, 1.05 eq) was heated neat at 80° C. under argon for 17 h until a black precipitate is formed. The reaction was cooled to room temperature, and the resultant black mass was dissolved in ethyl acetate (500 mL). Water (200 mL) was added slowly at 0° C. to quench the reaction, and the biphasic layers were separated. The organic layer was then washed with water (2×150 mL) and brine (1×150 mL), dried (MgSO4), filtered, and evaporated in vacuo. Recrystallization from hexane gave 11.5 g (69.3%) of 2-bromo-1-(2,4,6-trichlorophenyl)ethanone as a fluffy white solid. 1H-NMR (DMSO-d6) δ 7.86 (s, 2H), 4.78 (s, 2H); Rf=0.28, 2% ethyl acetate-hexane.

1. customis formed
2. temperatureThe reaction was cooled to room temperature
3. customto quench
4. customthe reaction
5. customthe biphasic layers were separated
6. washThe organic layer was then washed with water (2×150 mL) and brine (1×150 mL)
7. dry with materialdried (MgSO4)
8. filtrationfiltered
9. customevaporated in vacuo
10. customRecrystallization from hexane

ORD record

ord-dc850625b8b14ce6b79a051dbf82e6a7

Source dataset

uspto-grants-2006_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07144885B2