Methanol → Methyl 4-bromo-2-(methylsulfonyl)benzoate

HRID 2390290Notes

Reaction equation

HRID 2390290 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([S:11]([CH3:14])(=[O:13])=[O:12])[CH:3]=1.S(=O)(=O)(O)O.[CH3:20]O>>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:20])=[O:7])=[C:4]([S:11]([CH3:14])(=[O:13])=[O:12])[CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 27610574-Bromo-2-methanesulfonylbenzoic acid

Product 1

HCID 53393139Methyl 4-bromo-2-(methylsulfonyl)benzoateYield 72%

Procedure

A suspension of 4-bromo-2-(methylsulphonyl)benzoic acid (5.00 g; 17.9 mmol) in MeOH (100 ml) was treated with conc. sulphuric acid and the resulting mixture was heated at reflux for 5 days. The mixture was concentrated under reduced pressure, the residue was dissolved in EtOAc then washed with water, twice with NaHCO3 (sat) then with brine, dried on MgSO4, filtered and concentrated to give the title compound as a yellow solid (4.00 g, 72%).

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux for 5 days
  3. concentrationThe mixture was concentrated under reduced pressure
  4. dissolutionthe residue was dissolved in EtOAc
  5. washthen washed with water, twice with NaHCO3 (sat)
  6. dry with materialwith brine, dried on MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-10fee52c43184a85a00800637e46a4c6
Source dataset
uspto-grants-2012_09
Patent number
US08273769B2

Reaction notes

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