Acetyl chloride → Methyl 3-bromo-5-hydroxybenzoate

HRID 1845262Notes

Reaction equation

HRID 1845262 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)(=O)C>CO>[CH3:12][O:6][C:5](=[O:7])[C:4]1[CH:8]=[C:9]([OH:11])[CH:10]=[C:2]([Br:1])[CH:3]=1

Participants

4

Reactant 2

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

Product 1

HCID 53216607Methyl 3-bromo-5-hydroxybenzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-bromo-5-hydroxybenzoic acid (3.41 g, 15 mmol) (J. Chem. Soc. 1955, 463) in anhydrous methanol (80 mL) was added acetyl chloride (2.56 mL, 36 mmol) at 0° C. The mixture was then heated under reflux overnight. The volatiles were removed in vacuo to afford the title compound.

Workup

  1. temperatureThe mixture was then heated
  2. temperatureunder reflux overnight
  3. customThe volatiles were removed in vacuo

Sources & evidence

ORD record
ord-fd0f1a158cc048039864667c2bae6daf
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

Loading…