Reaction #84533

Reaction equation

N-(3-fluoro-4-morpholinophenyl)-3-oxobutanamide

Br2

→

title compound

Yield 47.0%

4-bromo-N-(3-fluoro-4-morpholinophenyl)-3-oxobutanamide

Yield 47.0%

Solvents

AcOH

Conditions

Workup

1. 1
   workup.ADDITIONAt end of addition
2. 2
   ConcentrationThe mixture was then concentrated in vacuo and 40 mL of water
3. 3
   workup.ADDITIONwas added
4. 4
   ExtractionThe resulting mixture was extracted with EtOAc (30 mL×4)
5. 5
   WashThe combined organic phases were washed with brine (40 mL×3)
6. 6
   Dryingdried over anhydrous Na2SO4
7. 7
   Concentrationconcentrated in vacuo
8. 8
   OtherThe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=2:1)

Procedure

To a solution of N-(3-fluoro-4-morpholinophenyl)-3-oxobutanamide (11.2 g, 40.0 mmol) and AcOH (100 mL) under N2 was added Br2 (2.4 mL) at rt. At end of addition, the mixture was stirred further at rt for 24 h. The mixture was then concentrated in vacuo and 40 mL of water was added. The resulting mixture was extracted with EtOAc (30 mL×4). The combined organic phases were washed with brine (40 mL×3), dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=2:1) to give the title compound as a yellow solid (6.80 g, 47%).

Source