Methanol → Methyl 4-bromo-3-methylbenzoate

HRID 2215109Notes

Reaction equation

HRID 2215109 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-6011e2e3481847e5abd2c762f30267bc
Source dataset
uspto-grants-2006_09
Patent number
US07109193B2

Reaction notes

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