Methanol → Methyl 2-Bromo-3-methylbenzoate

HRID 1814767Notes

Reaction equation

HRID 1814767 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-methylbenzoic 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-8412265d1db644c5b6721a2d3437a3a1
Source dataset
uspto-grants-2005_04
Patent number
US06878707B2

Reaction notes

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