Methanol → Methyl 4-bromo-2-ethylbenzoate

HRID 1438262Notes

Reaction equation

HRID 1438262 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%).

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-2ae7c1eff488433b8cf0e55554310993
Source dataset
uspto-grants-2009_11
Patent number
US07622605B2

Reaction notes

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