Lithium iodide → 2,6-Dichloro-4-cyanobenzoic acid

HRID 449899Notes

Reaction equation

HRID 449899 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([C:12]#[N:13])[CH:9]=[C:8]([Cl:14])[C:3]=1[C:4]([O:6]C)=[O:5].[Li+].[I-]>N1C=CC=CC=1>[Cl:1][C:2]1[CH:11]=[C:10]([C:12]#[N:13])[CH:9]=[C:8]([Cl:14])[C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 66321Lithium iodideHCID 53401291Methyl 2,6-dichloro-4-cyanobenzoate

Product 1

HCID 178550602,6-Dichloro-4-cyanobenzoic acidYield 73.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of methyl 2,6-dichloro-4-cyanobenzoate (160 g, 694 mmol) in pyridine (1.5 L) at room temperature was added LiI (186 g, 1.39 mol). The mixture was heated under reflux for 2 hours, cooled to room temperature and concentrated under reduced pressure. The residue was treated with 2 N HCl (1 L) and the resulting precipitate was collected by filtration. The solid was recrystallized from DMF and water to give 2,6-dichloro-4-cyanobenzoic acid (110 g, yield: 73%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 8.18 (s, 2H). LCMS (ESI) m/z: 216.0 [M+H+].

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. concentrationconcentrated under reduced pressure
  4. additionThe residue was treated with 2 N HCl (1 L)
  5. filtrationthe resulting precipitate was collected by filtration
  6. customThe solid was recrystallized from DMF and water

Sources & evidence

ORD record
ord-4f2ecd09651e4eaaa37edec68de86fe4
Source dataset
uspto-grants-2013_07
Patent number
US08486950B2

Reaction notes

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