Hydrochloric Acid → Methyl 4-Bromo-2-chlorobenzoate

HRID 1957476Notes

Reaction equation

HRID 1957476 reaction equation
Cl.[Br:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[C:5]([Cl:12])[CH:4]=1.[CH3:13]O>C(OCC)C>[Br:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([O:9][CH3:13])=[O:8])=[C:5]([Cl:12])[CH:4]=1

Participants

5

Reactant 3

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

Product 1

HCID 22058730Methyl 4-Bromo-2-chlorobenzoateYield 94%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Hydrochloric acid (gas) was bubbled through a solution of 10 g (42.5 mmol) of 4-bromo-2-chloro benzoic acid in 100 ml of methanol until reflux occurred. The resulting reaction mixture was allowed to react overnight. When the reaction was substantially complete, as indicated by TLC, the reaction mixture was concentrated in vacuo to provide a residue. This residue was redissolved in diethyl ether and washed sequentially with water (twice) and a saturated sodium chloride solution, dried over sodium sulfate, filtered and then concentrated in vacuo to provide 10 g of a light tan oil.

Workup

  1. temperatureuntil reflux
  2. customThe resulting reaction mixture
  3. customto react overnight
  4. concentrationthe reaction mixture was concentrated in vacuo
  5. customto provide a residue
  6. washwashed sequentially with water (twice) and a saturated sodium chloride solution
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-145ba7eb66a44b1ca01e2ce3eaac519b
Source dataset
uspto-grants-1998_07
Patent number
US05786325

Reaction notes

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