Dimethyl Sulfoxide → (2-Bromophenyl)(4-chlorophenyl)methanone

Temperature

-78 °C

To a solution of 2-bromobenzaldehyde (3.15 mL, 27.0 mmol) and THF (135 mL) at 0° C. was added (4-chlorophenyl)magnesium bromide solution (29.7 mL, 1M in THF, 29.7 mmol). The reaction was stirred at 0° C. for 30 min before addition of a saturated solution of ammonium chloride. The layers were separated and the aqueous extracted with EtOAc. The combined organics were washed with brine, dried over Na2SO4, filtered, and concentrated. The crude residue was purified via Biotage to afford (2-bromophenyl)(4-chlorophenyl)methanol. To a solution of DCM (100 mL) and oxalyl chloride (2.471 mL, 28.2 mmol) at −78° C. was added DMSO (3.34 mL, 47.0 mmol) and the reaction stirred at −78° C. for 15 min. After 15 min a solution of (2-bromophenyl)(4-chlorophenyl)methanol in DCM (25 mL) was added dropwise and stirred for 15 min at −78° C. before addition of Et3N (9.84 mL, 70.6 mmol). The cold bath was removed and the reaction was warmed to room temperature. To this solution was added water and the layers separated. The aqueous was extracted with DCM and the combined organics were dried over Na2SO4, filtered, and concentrated. The crude residue was purified via Biotage (EtOAc/hex) to afford (2-bromophenyl)(4-chlorophenyl)methanone. LC/MS m/z 295 [M+H]+.

1. customThe cold bath was removed
2. temperaturethe reaction was warmed to room temperature
3. additionTo this solution was added water
4. customthe layers separated
5. extractionThe aqueous was extracted with DCM
6. dry with materialthe combined organics were dried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated
9. customThe crude residue was purified via Biotage (EtOAc/hex)

ORD record

ord-06504732a41a4fa6bf2e7131a67be989

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08796261B2