Bromine → Benzoic acid, 2-bromo-5-ethoxy-4-methyl-, ethyl ester

HRID 402764Notes

Reaction equation

HRID 402764 reaction equation
[CH2:1]([O:3][C:4]1[C:5]([CH3:15])=[CH:6][CH:7]=[C:8]([CH:14]=1)[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH3:2].[Br:16]Br>C(O)(=O)C.O>[Br:16][C:7]1[CH:6]=[C:5]([CH3:15])[C:4]([O:3][CH2:1][CH3:2])=[CH:14][C:8]=1[C:9]([O:11][CH2:12][CH3:13])=[O:10]

Participants

5

Reactant 2

HCID 24408BromineHCID 23136282HCID 23136282, compound

Product 1

HCID 66764786Benzoic acid, 2-bromo-5-ethoxy-4-methyl-, ethyl esterYield 92.9%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of ethyl 5-ethoxy-4-methylbenzoate (500 mg, 2.40 mmol) in acetic acid (10 mL) and water (10 mL) at room temperature was added bromine (385 mg, 2.40 mmol). The resulting reaction mixture was stirred at 60° C. for 1 hour. After cooling to room temperature, the reaction mixture was diluted with hexanes/ether (80/20). Layers were separated and the organic layer was washed with saturated Na2CO3, brine, dried over Na2SO4, filtered and concentrated. The residue was purified on a silica gel column eluting with 5 to 10% EtOAc in hexanes to yield the title intermediate (660 mg, 2.23 mmol) as light yellow solid.

Workup

  1. customThe resulting reaction mixture
  2. temperatureAfter cooling to room temperature
  3. customLayers were separated
  4. washthe organic layer was washed with saturated Na2CO3, brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified on a silica gel column
  9. washeluting with 5 to 10% EtOAc in hexanes

Sources & evidence

ORD record
ord-a48448456db547b6b2aaeb906af84537
Source dataset
uspto-grants-2014_06
Patent number
US08742110B2

Reaction notes

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