Ammonium Chloride → 1-(4-Bromo-2-fluorophenyl)ethan-1-one

4-[(4-Bromo-2-flourophenyl)carbonyl]morpholine (5.06 g, 17.6 mmol, 1.00 equiv) was dissolved in 150 mL of THF and the resultant solution was cooled to 0° C. Methyl magnesium bromide (17.6 mL, 3.0 M in Et2O, 52.7 mmol, 3.00 equiv) was added over 5 minutes via syringe. The reaction mixture was maintained for 30 minutes, an additional portion of methyl magnesium bromide was added (10 mL, 29.9 mmol, 1.70 equiv) and the reaction mixture was allowed to warm to room temperature. After an additional 1.5 h, the reaction mixture was poured into saturated NH4Cl. The mixture was diluted with EtOAc and the phases were separated. The organic phase was washed with 1N HCl, saturated NaHCO3, and saturated NaCl, then dried over Na2SO4, filtered and concentrated en vacuo. The resulting residue was purified by column chromatography (40 g SiO2, 0→10% EtOAc/Hexanes) to afford 2.59 g (68%) of a colorless oil. 1H NMR (CDCl3) 7.79 (t, J=8.2 Hz, 1H, ), 7.42-7.36 (m, 2H), 2.66 (d, J=5.0 Hz, 3H).

1. temperatureThe reaction mixture was maintained for 30 minutes
2. customthe phases were separated
3. washThe organic phase was washed with 1N HCl, saturated NaHCO3, and saturated NaCl
4. dry with materialdried over Na2SO4
5. filtrationfiltered
6. concentrationconcentrated en vacuo
7. customThe resulting residue was purified by column chromatography (40 g SiO2, 0→10% EtOAc/Hexanes)

ORD-Eintrag

ord-93ad3771e55e424e9027c8cdd09f434e

Quelldatensatz

uspto-grants-2008_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07432258B2