Methanol → Methyl 4-bromo-2-methylbenzoate

HRID 2069825Notes

Reaction equation

HRID 2069825 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([CH3:11])[CH:3]=1.S(=O)(=O)(O)O.[CH3:17]O>>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:17])=[O:7])=[C:4]([CH3:11])[CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 995704-Bromo-2-methylbenzoic acid

Product 1

HCID 22031226Methyl 4-bromo-2-methylbenzoate

Procedure

4-bromo-2-methylbenzoic acid (100.04 g, 465 mmol), 500 mL of anhydrous methanol, and 5 mL of concentrated sulfuric acid were stirred at reflux under nitrogen for 24 hr. Cooled to room temperature and concentrated in vacuo. Diluted the residue with 500 mL EtOAc and washed with 200 mL 1 M aqueous NaOH, 200 mL water, and 200 mL brine. Dried the solution over MgSO4 and concentrated in vacuo to obtain methyl 4-bromo-2-methylbenzoate as a clear colorless liquid (100.06 g, 437 mmol). 1H NMR (300 MHz, chloroform-d) ppm 2.59 (s, 3 H) 3.89 (s, 3 H) 7.39 (d, J=8.29 Hz, 1 H) 7.42 (s, 1 H) 7.79 (d, J=8.67 Hz, 1 H).

Workup

  1. temperatureat reflux under nitrogen for 24 hr
  2. concentrationconcentrated in vacuo
  3. additionDiluted the residue with 500 mL EtOAc
  4. washwashed with 200 mL 1 M aqueous NaOH, 200 mL water, and 200 mL brine
  5. dry with materialDried the solution over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-03d11300f6ff4803948ba327c88e4066
Source dataset
uspto-grants-2012_10
Patent number
US08299077B2

Reaction notes

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