Ethanol → Ethyl 2-bromo-5-methoxybenzoate

HRID 1049502Notes

Reaction equation

HRID 1049502 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH2:13](O)[CH3:14]>S(=O)(=O)(O)O>[Br:1][C:2]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:3]=1[C:4]([O:6][CH2:13][CH3:14])=[O:5]

Participants

4

Reactant 2

HCID 702EthanolHCID 899062-Bromo-5-methoxybenzoic acid

Product 1

HCID 43389585Ethyl 2-bromo-5-methoxybenzoate

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Conditions

Temperature
95 °C

Procedure

To a solution of 2-bromo-5-methoxybenzoic acid (5.00 g) in ethanol (100 mL) was added conc. sulfuric acid (10 drops), and the mixture was stirred at 95° C. for 40.5 hr. The reaction mixture was concentrated under reduced pressure and water was added. The reaction mixture was extracted with ethyl acetate, and the extract was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (5.37 g) as a colorless oil.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure and water
  2. additionwas added
  3. extractionThe reaction mixture was extracted with ethyl acetate
  4. washthe extract was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-a70e10c0f3ee43aea3dc2ac7e8b225fd
Source dataset
uspto-grants-2016_07
Patent number
US09382188B2

Reaction notes

Loading…