Methanol → Methyl 3-bromo-4-hydroxybenzoate

HRID 1420834Notes

Reaction equation

HRID 1420834 reaction equation
S(=O)(=O)(O)O.[Br:6][C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][C:15]=1[OH:16])[C:10]([OH:12])=[O:11].[CH3:17]O>>[CH3:17][O:11][C:10](=[O:12])[C:9]1[CH:13]=[CH:14][C:15]([OH:16])=[C:7]([Br:6])[CH:8]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 843683-Bromo-4-hydroxybenzoic acid

Product 1

HCID 4778958Methyl 3-bromo-4-hydroxybenzoateYield 83%

Procedure

Sulfuric acid (conc., 10 ml) was added to a solution of 3-bromo-4-hydroxybenzoic acid (10.0 g, 46 mmol) in methanol (100 ml) and the mixture was stirred at room temperature for 72 h. The solvent was evaporated under reduced pressure and the residue was dissolved in ethyl acetate (250 ml). The mixture was washed with saturated aqueous sodium bicarbonate (2×250 ml), dried (MgSO4) and the solvent was evaporated under reduced pressure to give the title compound as a colorless solid (8.83 g, 83%). 1H NMR (250 MHz, CDCl3) δ8.19 (1 H, d, J 2.0 Hz), 7.92 (1 H, dd, J 8.5, 2.0 Hz), 7.05 (1 H, d, J 8.5 Hz), 5.91 (1 H, s), and 3.90 (3 H, s).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. dissolutionthe residue was dissolved in ethyl acetate (250 ml)
  3. washThe mixture was washed with saturated aqueous sodium bicarbonate (2×250 ml)
  4. dry with materialdried (MgSO4)
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-850966696ef54ff5a67857b52781a22a
Source dataset
uspto-grants-2000_06
Patent number
US06071927

Reaction notes

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