HCID 22117812, compound → 1-(3-Bromo-4-chlorophenyl)ethan-1-one

Temperature

-5 °C

A solution of 3-bromo-4-chloro-N-methoxy-N-methylbenzamide 105 (2.04 g, 7.3 mmol), was dissolved in 30 mL of dry THF. The solution was chilled to −5° C. in a salt bath under N2. Via syringe, methylmagnesium bromide (2.7 mL, 8.1 mmol) was added slowly to the solution. The solution was stirred for 2 h at −5° C., and then it was warmed to room temperature where it was stirred for another 1 h. The reaction was quenched with saturated NH4Cl, and it was diluted with ether and water. The organic solution was extracted with water and brine. The organic phase was dried over MgSO4, filtered, and concentrated in vacuo. The crude material was then filtered through a bed of silica and the filtrate was concentrated to give 1-(3-bromo-4-chlorophenyl)ethanone 106 (1.55 g, 91% yield) as a white solid.

1. temperatureit was warmed to room temperature where it
2. stirringwas stirred for another 1 h
3. customThe reaction was quenched with saturated NH4Cl, and it
4. additionwas diluted with ether and water
5. extractionThe organic solution was extracted with water and brine
6. dry with materialThe organic phase was dried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. filtrationThe crude material was then filtered through a bed of silica
10. concentrationthe filtrate was concentrated

ORD record

ord-1399b6cc26434366ac27f4cfcbf9358c

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08349831B2