Dimethylformamide → Methyl 4-(3-bromophenyl)-2-oxobut-3-enoate

HRID 2207918Notes

Reaction equation

HRID 2207918 reaction equation
[K+].[Br:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11](=[O:15])[C:12]([O-:14])=[O:13])[CH:6]=[CH:7][CH:8]=1.CI.[CH3:18]N(C)C=O>O>[CH3:18][O:13][C:12](=[O:14])[C:11](=[O:15])[CH:10]=[CH:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([Br:2])[CH:4]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 118431862HCID 118431862, compound

Product 1

HCID 70700454Methyl 4-(3-bromophenyl)-2-oxobut-3-enoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

4-(3-Bromo-phenyl)-2-oxo-3-butenoic acid potassium salt (41.0 g, 140.0 mmol) prepared in Step 1 and methyl iodide (15.0 mL, 238.0 mmol) were added to N,N-dimethylformamide (200.0 mL). The reaction mixture was stirred at 75° C. for 4 hours and then distilled water was added thereto. The reaction mixture was extracted with ethyl acetate. The extract was washed with a saturated solution of sodium hydrogen carbonate and brine, dried on anhydrous magnesium sulfate, and then concentrated under reduced pressure to give a yellow liquid residue. The resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/8) to give 10.0 g of the titled compound as a pale yellow solid.

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate
  2. washThe extract was washed with a saturated solution of sodium hydrogen carbonate and brine
  3. dry with materialdried on anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customto give a yellow liquid residue
  6. customThe resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/8)

Sources & evidence

ORD record
ord-2dd5e3c7d7c641de92c9514a2b4c3c83
Source dataset
uspto-grants-2016_06
Patent number
US09376420B2

Reaction notes

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