Methanol → Methyl 4-Bromo-3-hydroxybenzoate

HRID 2100375Notes

Reaction equation

HRID 2100375 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[OH:11].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])=[CH:4][C:3]=1[OH:11]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 64209734-Bromo-3-hydroxybenzoic acid

Product 1

HCID 6425184Methyl 4-Bromo-3-hydroxybenzoate

Procedure

4-Bromo-3-hydroxybenzoic acid (1 g) was dissolved in methanol (25 ml), concentrated sulphuric acid (165 μl) added and the reaction heated at reflux for 16 hours under nitrogen. The solvent was evaporated and ethyl acetate:chloroform (1:1, 100 ml) added. The solution was neutralised using aqueous sodium hydroxide solution (2M), washed with water (2×100 ml), dried using a hydrophobic filter and the solvent evaporated to leave methyl 4-bromo-3-hydroxybenzoate as a white solid (1.04 g).

Workup

  1. temperaturethe reaction heated
  2. temperatureat reflux for 16 hours under nitrogen
  3. customThe solvent was evaporated
  4. additionethyl acetate:chloroform (1:1, 100 ml) added
  5. washwashed with water (2×100 ml)
  6. customdried
  7. filtrationa hydrophobic filter
  8. customthe solvent evaporated

Sources & evidence

ORD record
ord-d0f46c5273904712a920ab55862ad4be
Source dataset
uspto-grants-2009_08
Patent number
US07572790B2

Reaction notes

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