Methanol → Benzoic acid, 4-bromo-3,5-dihydroxy-, methyl ester

HRID 1643539Notes

Reaction equation

HRID 1643539 reaction equation
[Br:1][C:2]1[C:10]([OH:11])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[OH:12].OS(O)(=O)=O.[CH3:18]O>>[CH3:18][O:7][C:6](=[O:8])[C:5]1[CH:9]=[C:10]([OH:11])[C:2]([Br:1])=[C:3]([OH:12])[CH:4]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 860234-Bromo-3,5-dihydroxybenzoic acid

Product 1

HCID 118602Benzoic acid, 4-bromo-3,5-dihydroxy-, methyl esterYield 100%

Procedure

To a solution of 4-bromo-3,5-dihydroxybenzoic acid (13.89 g, 59.6 mmol) in methanol (50 mL) was added H2SO4 (concentrated, 1 mL). The reaction mixture was heated to reflux overnight. The mixture was quenched with H2O (500 mL) and extracted with 10% MeOH in CH2Cl2 (5×500 mL), dried over MgSO4 and concentrated in vacuo to give a white solid (14.8 g, 100% yield). 1H NMR (400 MHz, DMSO-d6) δ 10.47 (s, 2 H) 7.00 (s, 2 H) 3.80 (s, 3 H); LCMS for C8H7BrO4 m/z 249.10 (M+H)+.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux overnight
  3. customThe mixture was quenched with H2O (500 mL)
  4. extractionextracted with 10% MeOH in CH2Cl2 (5×500 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-eda1555e5eb74717a11d5eb5b5cefa57
Source dataset
uspto-grants-2012_02
Patent number
US08119624B2

Reaction notes

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