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

HRID 56255Notes

Reaction equation

HRID 56255 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:14][C:15](=[O:20])[CH2:16][C:17](=[O:19])[CH3:18])[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1.[Br:21]Br>CC(O)=O>[Br:21][CH2:18][C:17](=[O:19])[CH2:16][C:15]([NH:14][C:4]1[CH:5]=[CH:6][C:7]([N:8]2[CH2:9][CH2:10][O:11][CH2:12][CH2:13]2)=[C:2]([F:1])[CH:3]=1)=[O:20]

Participants

4

Reactant 2

HCID 24408BromineHCID 90023295N-(3-fluoro-4-morpholinophenyl)-3-oxobutanamide

Product 1

HCID 900232464-bromo-N-(3-fluoro-4-morpholinophenyl)-3-oxobutanamideYield 47%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

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%).

Workup

  1. additionAt end of addition
  2. concentrationThe mixture was then concentrated in vacuo and 40 mL of water
  3. additionwas added
  4. extractionThe resulting mixture was extracted with EtOAc (30 mL×4)
  5. washThe combined organic phases were washed with brine (40 mL×3)
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=2:1)

Sources & evidence

ORD record
ord-f607e72a2b3a4f3a997b4dde90475ebc
Source dataset
uspto-grants-2016_09
Patent number
US09434695B2

Reaction notes

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