Methanol → Methyl 3-bromo-4-ethylbenzoate

HRID 1434575Notes

Reaction equation

HRID 1434575 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH2:11][CH3:12])[C:5]([OH:7])=[O:6].OS(O)(=O)=O.[CH3:18]O>>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH2:11][CH3:12])[C:5]([O:7][CH3:18])=[O:6]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 73033683-bromo-4-ethylbenzoic acid

Product 1

HCID 13877473Methyl 3-bromo-4-ethylbenzoate

Procedure

3-Bromo-4-ethyl-benzoic acid (D43) (19.40 g) was dissolved in MeOH (200 mL) and then treated with conc. H2SO4 (1 mL). The mixture was heated at reflux overnight, and then concentrated under reduced pressure. The residue was partitioned between EtOAc and saturated aqueous NaHCO3 solution, extracting again with EtOAc. The combined extracts were then washed with brine, dried (MgSO4). The solvent was evaporated in vacuo to afford the title compound (15.8 g). 1H NMR (CDCl3) δ 1.24 (3H, t), 2.79 (2H, q), 3.91 (3H, s), 7.29 (1H, d), 7.89 (1H, dd), 8.19 (1H, d).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux overnight
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was partitioned between EtOAc and saturated aqueous NaHCO3 solution
  5. extractionextracting again with EtOAc
  6. washThe combined extracts were then washed with brine
  7. dry with materialdried (MgSO4)
  8. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-3adc8d2dfc3c40c3a0c56e97f84ec88a
Source dataset
uspto-grants-2009_11
Patent number
US07615550B2

Reaction notes

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