Hydrochloric Acid → Methyl 4-Bromo-2-chlorobenzoate

HRID 1026575Notes

Reaction equation

HRID 1026575 reaction equation
[CH3:1]O.[Br:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[C:6]([Cl:13])[CH:5]=1.Cl>O1CCOCC1>[Br:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]([O:10][CH3:1])=[O:9])=[C:6]([Cl:13])[CH:5]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 1088294-Bromo-2-chlorobenzoic acid

Product 1

HCID 22058730Methyl 4-Bromo-2-chlorobenzoate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a methanol solution (25 ml) of 4-bromo-2-chlorobenzoic acid (5.0 g) was added hydrochloric acid/a 1,4-dioxane solution (4 N, 25 ml), followed by heating at reflux for 90 minutes. The reaction solution was brought back to room temperature, and concentrated under reduced pressure. Dichloromethane and a saturated aqueous sodium hydrogen carbonate solution were added to the residue, and the solution was separated. The organic layer was washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to afford methyl 4-bromo-2-chlorobenzoate (5.3 g).

Workup

  1. temperatureby heating
  2. temperatureat reflux for 90 minutes
  3. customwas brought back to room temperature
  4. concentrationconcentrated under reduced pressure
  5. additionDichloromethane and a saturated aqueous sodium hydrogen carbonate solution were added to the residue
  6. customthe solution was separated
  7. washThe organic layer was washed with saturated sodium chloride solution
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d295ede117584bf9b0ed3191a8508393
Source dataset
uspto-grants-2014_05
Patent number
US08729095B2

Reaction notes

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