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

HRID 1442812Notes

Reaction equation

HRID 1442812 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>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](=[O:14])[CH2:9][CH2:10][C:11]([O:13][CH3:20])=[O:12])=[CH:6][CH:7]=1

Participants

4

Reactant 3

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

Product 1

HCID 838865Methyl 4-(4-bromophenyl)-4-oxobutanoateYield 89%

Procedure

To a solution of 4-(4-bromophenyl)-4-oxobutanoic acid (16.0 g, 62.0 mmol) in MeOH (200 mL) was added concentrated H2SO4 (0.2 mL). The mixture was heated at reflux overnight. The solvent was evaporated and then water (250 mL) was added to the residue. The mixture was neutralized with sat. NaHCO3 solution until pH 7-8. The mixture was extracted with ethyl acetate (100 mL×2). The combined organics were washed with brine, dried over anhydrous Na2SO4, and concentrated in vacuo to afford methyl 4-(4-bromophenyl)-4-oxobutanoate (15.0 g, 89%). 1H NMR (CDCl3, 300 MHz) δ 7.85 (d, J=8.1, 1H), 7.61 (d, J=8.1, 2H), 3.71 (s, 3H), 3.28 (t, J=6.6, 2H), 2.77 (t, J=6.6, 2H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux overnight
  3. customThe solvent was evaporated
  4. additionwater (250 mL) was added to the residue
  5. extractionThe mixture was extracted with ethyl acetate (100 mL×2)
  6. washThe combined organics were washed with brine
  7. dry with materialdried over anhydrous Na2SO4
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-36c4cb25db4b4158a2306cd0694a2504
Source dataset
uspto-grants-2010_02
Patent number
US07659268B2

Reaction notes

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