Methanol → Methyl 4-Bromo-3-hydroxybenzoate

HRID 1158393Notes

Reaction equation

HRID 1158393 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].[CH3:12]O>OS(O)(=O)=O>[CH3:12][O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([Br:1])=[C:3]([OH:11])[CH:4]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 64209734-Bromo-3-hydroxybenzoic acid

Product 1

HCID 6425184Methyl 4-Bromo-3-hydroxybenzoate

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a solution of 4-bromo-3-hydroxy-benzoic acid (prepared according to J. Amer. Chem Soc. 1946, 68, 574) (5 g, 32.8 mmol) in MeOH (100 mL), conc. H2SO4 (1 mL) is added. The solution is refluxed for 14 h, then concentrated to about 30 mL and poured into a water. The aqueous layer is extracted with ether (50 mL×4) and the combined organic extracts are neutralized with a saturated aqueous solution of NaHCO3 (50 mL×2), washed with brine (50 mL), dried over Na2SO4, filtered and concentrated to give the title compound as a white powder. TLC, Rf (AcOEt)=0.9. 1H-NMR (CDCl3, 300 MHz): δ=5.8 (bs, 1H), 7.45 (d, 1H), 7.55 (d, 1H), 7.7 (s, 1H) ppm.

Workup

  1. temperatureThe solution is refluxed for 14 h
  2. concentrationconcentrated to about 30 mL
  3. additionpoured into a water
  4. extractionThe aqueous layer is extracted with ether (50 mL×4)
  5. washwashed with brine (50 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-467bf18bc8c44104a3ead73bcfff9432
Source dataset
uspto-grants-2010_10
Patent number
US07807709B2

Reaction notes

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