Methanol → Methyl 2-(3-bromo-4-methoxyphenyl)acetate

HRID 2410133Notes

Reaction equation

HRID 2410133 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:10][C:11]([OH:13])=[O:12])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].OS(O)(=O)=O.[CH3:19]O>>[CH3:19][O:12][C:11](=[O:13])[CH2:10][C:4]1[CH:5]=[CH:6][C:7]([O:8][CH3:9])=[C:2]([Br:1])[CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 1366153-Bromo-4-methoxyphenylacetic acid

Product 1

HCID 12717575Methyl 2-(3-bromo-4-methoxyphenyl)acetate

Procedure

A solution of 3-bromo-4-methoxyphenylacetic acid (7.5 g, 30.6 mmol), MeOH (24 mL) and H2SO4 (0.8 mL) was stirred at 75° C. for 17 h. The reaction mixture was concentrated. The residue was poured into H2O and extracted with CH2Cl2. The organic layer was washed with brine, dried (NaSO4), filtered and concentrated to afford the title compound. tR: 0.99 min (LC-MS 2).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionThe residue was poured into H2O
  3. extractionextracted with CH2Cl2
  4. washThe organic layer was washed with brine
  5. dry with materialdried (NaSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-b914f0130cb9462b8ef8b77c077ecaa6
Source dataset
uspto-grants-2014_08
Patent number
US08815926B2

Reaction notes

Loading…