Methanol → Methyl 2-(4-bromophenyl)acetate

HRID 2076579Notes

Reaction equation

HRID 2076579 reaction equation
S(=O)(=O)(O)O.[Br:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C:14]([OH:16])=[O:15])=[CH:9][CH:8]=1.[CH3:17]O>>[Br:6][C:7]1[CH:8]=[CH:9][C:10]([CH2:13][C:14]([O:16][CH3:17])=[O:15])=[CH:11][CH:12]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 74654Benzeneacetic acid, 4-bromo-

Product 1

HCID 316783Methyl 2-(4-bromophenyl)acetateYield 100%

Procedure

Concentrated sulfuric acid (30 ml) was added to a solution of (4-bromophenyl)acetic acid (101 g, 468 mmol) in methanol (1000 ml) under ice-cooling and the mixture was stirred at room temperature for 2 hours. After the reaction mixture was concentrated and ethyl acetate was added to the residue, the mixture was successively washed with water, a saturated aqueous sodium hydrogencarbonate solution and a saturated aqueous NaCl solution and dried with anhydrous sodium sulfate. The residue obtained by removing the solvent under reduced pressure was purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=5/1) to give methyl (4-bromophenyl)acetate (107 g, yield: 100%).

Workup

  1. temperaturecooling
  2. concentrationAfter the reaction mixture was concentrated
  3. additionethyl acetate was added to the residue
  4. washthe mixture was successively washed with water
  5. dry with materiala saturated aqueous sodium hydrogencarbonate solution and a saturated aqueous NaCl solution and dried with anhydrous sodium sulfate
  6. customThe residue obtained
  7. customby removing the solvent under reduced pressure
  8. customwas purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-65989111f6e546ebafc8acce35d49c70
Source dataset
uspto-grants-2011_04
Patent number
US07923573B2

Reaction notes

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