Chlorosuccinimide → methyl 2,5-dichloro-4-hydroxybenzoate

HRID 1166715Notes

Reaction equation

HRID 1166715 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([OH:12])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[Cl:13]N1C(=O)CCC1=O>C(O)(=O)C>[Cl:1][C:2]1[CH:11]=[C:10]([OH:12])[C:9]([Cl:13])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 134988302-Chloro-4-hydroxy-benzoic acid methyl ester

Product 1

HCID 11127832methyl 2,5-dichloro-4-hydroxybenzoateYield 60%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of methyl 2-chloro-4-hydroxybenzoate (13.6 g, 73.1 mmol) in acetic acid (300 mL) was added N-chlorosuccinimide (9.8 g, 73.7 mmol). The solution was refluxed for 24 h and the solvent was evaporated under vacuo. The residue was taken up in chloroform, washed with water, brine, dried over magnesium sulfate, filtered and concentrated. Methyl 2,3-dichloro-4-hydroxybenzoate precipitated out of ethyl acetate. Chromatography of the residue using ethyl acetate/hexane (1/9 to 3/7) afforded methyl 2,5-dichloro-4-hydroxybenzoate (1.4 g, 60%) as well as an additional batch of methyl 2,3-dichloro-4-hydroxybenzoate isomer (total of 8.4 g, 10%).

Workup

  1. temperatureThe solution was refluxed for 24 h
  2. customthe solvent was evaporated under vacuo
  3. washwashed with water, brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customMethyl 2,3-dichloro-4-hydroxybenzoate precipitated out of ethyl acetate

Sources & evidence

ORD record
ord-12c041b6d19a42deaeb0adb40047582f
Source dataset
uspto-grants-2003_09
Patent number
US06613942B1

Reaction notes

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