Acetyl chloride → Methyl 3-bromo-5-hydroxybenzoate

HRID 1809514Notes

Reaction equation

HRID 1809514 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([OH:11])[CH:10]=1)[C:5]([OH:7])=[O:6].[C:12](Cl)(C)=O>CO.CC(=O)OCC>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([OH:11])[CH:10]=1)[C:5]([O:7][CH3:12])=[O:6]

Participants

5

Reactant 2

HCID 6367Acetyl chlorideHCID 157355113-Bromo-5-hydroxybenzoic acid

Product 1

HCID 53216607Methyl 3-bromo-5-hydroxybenzoateYield 98.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a flask containing 3-bromo-5-hydroxybenzoic acid (2.0 g, 9.2 mmol) in anhydrous MeOH (10 mL) at 0° C. under N2 was added AcCl (912 μL, 12.9 mmol). The reaction mixture was allowed to warm to room temperature overnight. The mixture was diluted with EA and washed with NaHCO3. The organic layers were dried and concentrated to provide 2.1 g (97%) of methyl 3-bromo-5-hydroxybenzoate as a white solid. LCMS-ESI (m/z) calculated for C8H7BrO3: 231.04; found 232.9 [M+H]+, tR=3.06 min.

Workup

  1. washwashed with NaHCO3
  2. customThe organic layers were dried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-396ac793181b4dae8987d8fba80edd43
Source dataset
uspto-grants-2013_01
Patent number
US08362048B2

Reaction notes

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