Methanol → Methyl 2,4-dibromobenzoate

HRID 541327Notes

Reaction equation

HRID 541327 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]([Br:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(=O)(=O)(O)O.[CH3:17]O>>[Br:1][C:2]1[CH:10]=[C:9]([Br:11])[CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH3:17])=[O:5]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 118962,4-Dibromobenzoic acid

Product 1

HCID 22572357Methyl 2,4-dibromobenzoate

Procedure

A solution of 2,4-dibromobenzoic acid (52.0 g, 176 mmol, 1.00 equiv, 95%) and sulfuric acid (20 mL) in methanol (400 mL) was stirred at 90° C. overnight. After cooling to room temperature, the mixture was concentrated under reduced pressure. The residue was diluted with 500 mL of ethyl acetate and washed with 3×100 mL of H2O followed by 1×100 mL of NaHCO3 (aq., sat. Note: gas evolution occurs). The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo. This resulted in 45.0 g (78%) of methyl 2,4-dibromobenzoate as a yellow oil.

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. additionThe residue was diluted with 500 mL of ethyl acetate
  3. washwashed with 3×100 mL of H2O
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThis resulted in 45.0 g (78%) of methyl 2,4-dibromobenzoate as a yellow oil

Sources & evidence

ORD record
ord-58aced2dc6a942bf94268b77546d5894
Source dataset
uspto-grants-2014_10
Patent number
US08871790B2

Reaction notes

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