Methanol → Methyl 2-Bromo-3-methylbenzoate

HRID 1531286Notes

Reaction equation

HRID 1531286 reaction equation
[Br:1][C:2]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH3:12]O>S(=O)(=O)(O)O>[Br:1][C:2]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH3:12])=[O:5]

Participants

4

Reactant 2

HCID 887MethanolHCID 27355882-Bromo-3-methylbenzoic acid

Product 1

HCID 10823279Methyl 2-Bromo-3-methylbenzoate

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of 2-bromo-3-methyl-benzoic acid (21.5 g, 100 mmol) in 500 mL of methanol and 8 mL of concentrated sulfuric acid is refluxed overnight. Methanol is removed under reduced pressure, the residue is taken up in ether, washed with sodium bicarbonate, brine, and dried over magnesium sulfate, filtered, and evaporated under reduced pressure to give methyl 2-bromo-3-methylbenzoate as an oil.

Workup

  1. customMethanol is removed under reduced pressure
  2. washwashed with sodium bicarbonate, brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-a40c02a9957543b49091a4472618b076
Source dataset
uspto-grants-2001_03
Patent number
US06197798B1

Reaction notes

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