Acetyl chloride → Methyl 4-bromo-2-methylbenzoate

HRID 424821Notes

Reaction equation

HRID 424821 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]([CH3:15])[CH:7]=1>CO.C(=O)([O-])[O-].[Na+].[Na+]>[CH3:1][O:11][C:10](=[O:12])[C:9]1[CH:13]=[CH:14][C:6]([Br:5])=[CH:7][C:8]=1[CH3:15]

Participants

5

Reactant 2

HCID 6367Acetyl chlorideHCID 995704-Bromo-2-methylbenzoic acid

Product 1

HCID 22031226Methyl 4-bromo-2-methylbenzoateYield 97.8%

Reagents, catalysts & solvents 2

HCID 10340Sodium CarbonateCatalystHCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

Acetyl chloride (199 mL, 2.79 mol) is added to a solution of 4-bromo-2-methylbenzoic acid (500 g, 2.32 mol) in methanol (2500 mL) at 5° C. The mixture is heated at 65° C. for 7 hours. The mixture is cooled to room temperature and sodium carbonate (19 g, 0.18 mol) is added. The reaction mixture is stirred for 15 minutes. The slurry is filtered and the filtrate is concentrated under reduced pressure. The resulting residue is partitioned between MTBE (400 mL) and water (400 mL). The organic phase is washed with brine, dried over magnesium sulfate, and concentrated to give the title compound (520 g) as a golden oil. ES/MS m/e 216 (M+1).

Workup

  1. temperatureThe mixture is cooled to room temperature
  2. filtrationThe slurry is filtered
  3. concentrationthe filtrate is concentrated under reduced pressure
  4. customThe resulting residue is partitioned between MTBE (400 mL) and water (400 mL)
  5. washThe organic phase is washed with brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-8c37df797f86476692c6f48588784854
Source dataset
uspto-grants-2012_01
Patent number
US08106077B2

Reaction notes

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