Ammonium Chloride → HCID 12319462, compound

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. m/z (ESI) 295, 297 [M+H]+.

1. customThe layers were separated
2. extractionthe aqueous extracted with EtOAc
3. washThe combined organics were washed with brine
4. dry with materialdried over Na2SO4
5. filtrationfiltered
6. concentrationconcentrated
7. customThe crude residue was purified via Biotage

ORD record

ord-f3f11070fc3b463fbd4ae280eae0dc92

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09249161B2