Methanol → Methyl 3-bromo-6-(phenylthio)-benzoate

HRID 435631Notes

Reaction equation

HRID 435631 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]([S:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].[CH3:18]O>S(=O)(=O)(O)O>[Br:1][C:2]1[CH:3]=[C:4]([C:8]([S:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[CH:9][CH:10]=1)[C:5]([O:7][CH3:18])=[O:6]

Participants

4

Reactant 2

HCID 887MethanolHCID 214560473-Bromo-6-(phenylthio)-benzoic acid

Product 1

HCID 21481147Methyl 3-bromo-6-(phenylthio)-benzoate

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

478 g of 3-bromo-6-(phenylthio)-benzoic acid in 1.5 litres of methanol and 200 ml of concentrated sulphuric acid are heated under reflux for 8 hours. The solution is concentrated under reduced pressure, treated with water and extracted with water. The organic solution is washed with aqueous sodium bicarbonate solution, dried over magnesium sulphate and concentrated under reduced pressure. There is obtained methyl 3-bromo-6-(phenylthio)-benzoate as a yellow oil.

Workup

  1. temperatureunder reflux for 8 hours
  2. concentrationThe solution is concentrated under reduced pressure
  3. additiontreated with water
  4. extractionextracted with water
  5. washThe organic solution is washed with aqueous sodium bicarbonate solution
  6. dry with materialdried over magnesium sulphate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ca0f3d8f232543b5b12f4da66edcf61d
Source dataset
uspto-grants-1977_02
Patent number
US04006145

Reaction notes

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