Methanol → Methyl 4-bromo-2-ethylbenzoate

HRID 2387069Notes

Reaction equation

HRID 2387069 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([CH2:11][CH3:12])[CH:3]=1.[CH3:13]O>OS(O)(=O)=O>[CH3:13][O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([Br:1])=[CH:3][C:4]=1[CH2:11][CH3:12]

Participants

4

Reactant 2

HCID 887MethanolHCID 106570054-Bromo-2-ethylbenzoic acid

Product 1

HCID 53797189Methyl 4-bromo-2-ethylbenzoate

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Conditions

Temperature
90 °C

Procedure

To a solution of 4-bromo-2-ethyl-benzoic acid (1.35 g, 5.89 mmol) in MeOH (40 mL) was added H2SO4 (1 drop). The mixture was stirred at 90° C. for 48 hours, at which time the volatiles were removed in vacuo. The residue was dissolved in Et2O, washed with satd NaHCO3 and brine, dried over MgSO4, and concentrated to a clear oil (1.01 g, 70%). 1H NMR (300 MHz, CDCl3): δ 1.22 (t, J=7.5 Hz, 3 H), 2.95 (q, J=7.5 Hz, 2 H), 3.87 (s, 3 H), 7.36 (dd, J=8.3, 2.1 Hz, 1 H), 7.42 (d, J=2.1 Hz, 1 H), 7.72 (d, J=8.3 Hz, 1 H).

Workup

  1. customwere removed in vacuo
  2. dissolutionThe residue was dissolved in Et2O
  3. washwashed with satd NaHCO3 and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated to a clear oil (1.01 g, 70%)

Sources & evidence

ORD record
ord-1df06247bae9429e8468678f9d93205f
Source dataset
uspto-grants-2012_09
Patent number
US08268835B2

Reaction notes

Loading…