Methanol → methyl 4-bromo-2-methylbutanoate

HRID 1695221Notes

Reaction equation

HRID 1695221 reaction equation
[Br:1][CH2:2][CH2:3][CH:4]([CH3:8])[C:5]([OH:7])=[O:6].[CH3:9]O>OS(O)(=O)=O>[CH3:9][O:6][C:5](=[O:7])[CH:4]([CH3:8])[CH2:3][CH2:2][Br:1]

Participants

4

Reactant 2

HCID 887Methanol2×HCID 2133316964805-71-6

Product 1

HCID 11745547methyl 4-bromo-2-methylbutanoate

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

4-Bromo-2-methyl-butyric acid (2.16 g, 1 eq, prepared according to the procedure described in J. Am. Chem. Soc. 1990, 112, 2755) was dissolved in MeOH (10 mL) and a few drops of conc. H2SO4 were added. The reaction was stirred at reflux for 16 hours. After reaction completion, as monitored by LC-MS, MeOH was removed under reduced pressure, the oily residue was diluted with water, the pH adjusted to 9 with 10% NaOH, and the product was extracted with Et2O (2×20 mL) and dried over Na2SO4. The title compound was obtained as a colourless oil (1.29 g, 55% yield) after solvent removal.

Workup

  1. temperatureat reflux for 16 hours
  2. customAfter reaction completion
  3. customwas removed under reduced pressure
  4. additionthe oily residue was diluted with water
  5. extractionthe product was extracted with Et2O (2×20 mL)
  6. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-d5c6090c33fe4d359128fb48e8792ec7
Source dataset
uspto-grants-2012_04
Patent number
US08163729B2

Reaction notes

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