(4-Bromo-3-fluorophenyl)(morpholin-4-yl)methanone → 1-(4-Bromo-3-fluorophenyl)ethan-1-one

To a 0° C. solution containing 8.62 g of 4-[(4-bromo-3-fluorophenyl)carbonyl]morpholine (30 mmols) in 150 mL THF was added 15 mL of methylmagnesium bromide (45 mmols, 3M solution in Et2O). The reaction mixture was allowed to warm slowly to ambient temperature. After 18 h the reaction mixture was quenched with 20 mL saturated aqueous NH4Cl solution. The layers were separated, and the organic layer was dried over MgSO4, filtered through a frit, and concentrated. The crude product was purified by silica gel chromatography (120 g redisep column, silica 40 um, 60A, 85 ml/min, A: EtOAc, B: hexanes, A: 8% for 14 min) to give 2.40 g (37%) of title compound as a yellow oil.

1. customAfter 18 h the reaction mixture was quenched with 20 mL saturated aqueous NH4Cl solution
2. customThe layers were separated
3. dry with materialthe organic layer was dried over MgSO4
4. filtrationfiltered through a frit
5. concentrationconcentrated
6. customThe crude product was purified by silica gel chromatography (120 g redisep column, silica 40 um, 60A, 85 ml/min

ORD record

ord-019d3314228947fd99c08ac4dd45c0ee

Source dataset

uspto-grants-2008_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07432258B2