Acetyl chloride → Methyl 4-Bromo-2-chlorobenzoate

HRID 1069062Notes

Reaction equation

HRID 1069062 reaction equation
[C:1](Cl)(=O)C.[Br:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[C:8]([Cl:15])[CH:7]=1>CO>[Br:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([O:12][CH3:1])=[O:11])=[C:8]([Cl:15])[CH:7]=1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 1088294-Bromo-2-chlorobenzoic acid

Product 1

HCID 22058730Methyl 4-Bromo-2-chlorobenzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To anhydrous methanol (45 mL) was added acetyl chloride (1.9 mL) over 2 min. The mixture, which became slightly exothermic and evolved gas, was stirred for 15 min. 4-Bromo-2-chlorobenzoic acid (3.0 g) was added in one portion and the mixture was heated at gentle reflux for 16 h. The mixture was allowed to cool to room temperature and the solvent was removed with a rotary evaporator. The residue was partitioned between saturated aqueous sodium bicarbonate and diethyl ether. The organic layer was separated, dried over sodium sulfate, filtered and concentrated to afford the title compound as a white solid (2.89 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat gentle reflux for 16 h
  3. customthe solvent was removed with a rotary evaporator
  4. customThe residue was partitioned between saturated aqueous sodium bicarbonate and diethyl ether
  5. customThe organic layer was separated
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-4e9d030bdd1241fdaf0f00d0324d1e34
Source dataset
uspto-grants-2001_06
Patent number
US06251925B1

Reaction notes

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