Methanol → Methyl 4-bromo-3-methylbenzoate

HRID 2184426Notes

Reaction equation

HRID 2184426 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[CH3:11].S(=O)(=O)(O)O.[CH3:17]O>>[CH3:17][O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([Br:1])=[C:3]([CH3:11])[CH:4]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 821314-Bromo-3-methylbenzoic acid

Product 1

HCID 3294148Methyl 4-bromo-3-methylbenzoate

Procedure

To a suspension of 4-bromo-3-methylbenzoic acid (10.0 g, 46.5 mmol) in methanol (125 mL) was added concentrated sulfuric acid (1 mL). The reaction was heated at reflux overnight with a homogeneous solution obtained after several minutes of heating. After cooling, the methanol was removed in vacuo and the residue was dissolved in dichloromethane and washed with saturated aqueous sodium bicarbonate. The organic phase was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give 10.2 g of title compound as a brown solid, m.p. 41-43° C.

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux overnight with a homogeneous solution
  3. customobtained after several minutes
  4. temperatureof heating
  5. temperatureAfter cooling
  6. customthe methanol was removed in vacuo
  7. dissolutionthe residue was dissolved in dichloromethane
  8. washwashed with saturated aqueous sodium bicarbonate
  9. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-aa6748c0dfc0425fa58ea3e526cec714
Source dataset
uspto-grants-2005_05
Patent number
US06900200B2

Reaction notes

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