Methanol → Methyl 4-(4-bromophenyl)-4-oxobutanoate

HRID 489218Notes

Reaction equation

HRID 489218 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:14])[CH2:9][CH2:10][C:11]([OH:13])=[O:12])=[CH:4][CH:3]=1.OS(O)(=O)=O.[CH3:20]O>>[CH3:20][O:12][C:11](=[O:13])[CH2:10][CH2:9][C:8]([C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=1)=[O:14]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 806463-(4-Bromobenzoyl)propionic acid

Product 1

HCID 838865Methyl 4-(4-bromophenyl)-4-oxobutanoate

Procedure

4-(4-Bromophenyl)-4-oxobutyric acid (86.4 g, 0.336 mol) (Preparation 1) in MeOH (1.7 l) containing H2SO4 (86 ml) was refluxed for 21 h. After cooling, the light precipitate was filtered off and the reaction mixture concentrated to dryness. The obtained solid was placed in water and extracted twice with EtOAc. The organic layer was washed with diluted NaOH and twice with brine, dried over Na2SO4 and concentrated to yield the desired 4-(4-bromophenyl)-4-oxobutyric acid methyl ester as a low melting point solid (87.5 g, mp=50° C.). 1H NMR (CDCl3): 7.85 (2H, d, J=8.5 Hz), 7.60 (2H, d, J=8.5 Hz), 3.71 (3H, s), 3.28 (2H, t, J=6.5 Hz), 2.76 (2H, t, J=6.5 Hz).

Workup

  1. temperaturewas refluxed for 21 h
  2. temperatureAfter cooling
  3. filtrationthe light precipitate was filtered off
  4. concentrationthe reaction mixture concentrated to dryness
  5. extractionextracted twice with EtOAc
  6. washThe organic layer was washed with diluted NaOH and twice with brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-1dc83b9f3d194ca2ab31fd69c18999ad
Source dataset
uspto-grants-2005_12
Patent number
US06977267B2

Reaction notes

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