Chlorosuccinimide → Methyl 3-chloro-5-cyano-4-hydroxybenzoate

HRID 385022Notes

Reaction equation

HRID 385022 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[OH:13])[C:6]([O:8][CH3:9])=[O:7])#[N:2].[Cl:14]N1C(=O)CCC1=O.Cl.C(OCC)(=O)C>C(Cl)(Cl)Cl.CO>[Cl:14][C:11]1[CH:10]=[C:5]([CH:4]=[C:3]([C:1]#[N:2])[C:12]=1[OH:13])[C:6]([O:8][CH3:9])=[O:7]

Participants

6

Reactant 3

HCID 31398ChlorosuccinimideHCID 11769089Methyl 3-cyano-4-hydroxybenzoateHCID 21866389Hydrogen chloride-ethyl acetate

Product 1

HCID 68108871Methyl 3-chloro-5-cyano-4-hydroxybenzoateYield 53.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

Methyl 3-cyano-4-hydroxybenzoate (2.00 g) was dissolved in chloroform (15 mL) and methanol (5 mL), and N-chlorosuccinimide (3.62 g) and 4N hydrochloric acid-ethyl acetate (6.8 mL) were added to the solution, and then the mixture was stirred at room temperature for 1 hour. The solvent was distilled off under reduced pressure and a mixture of methanol and water in a mixing ratio of 9:1 was added, and then the precipitated crystal was washed with water and isopropyl alcohol to obtain the title compound (1.27 g) as a colorless crystal.

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. additiona mixture of methanol and water in a mixing ratio of 9:1
  3. additionwas added
  4. washthe precipitated crystal was washed with water and isopropyl alcohol

Sources & evidence

ORD record
ord-97ab2f81be514fb6b61b27ff2a866bd9
Source dataset
uspto-grants-2013_02
Patent number
US08367843B2

Reaction notes

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