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

HRID 875411Notes

Reaction equation

HRID 875411 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].[I-].[Li+]>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 86%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A suspension of methyl 2,6-dichloro-4-cyanobenzoate (620 mg, 2.6 mmol) in pyridine (5 mL) was treated with anhydrous lithium iodide (1000 mg, 8 mmol). The resulting reaction mixture was stirred at reflux for 1 hour and concentrated under vacuum to remove pyridine. The residue was acidified with hydrochloric acid (2N) under ice-cold condition to adjust the pH between 2 to 3. The precipitated solid was filtered, washed with water and dried to yield 2,6-dichloro-4-cyanobenzoic acid (380 mg, 86%) as a pale brown solid.

Workup

  1. customThe resulting reaction mixture
  2. temperatureat reflux for 1 hour
  3. concentrationconcentrated under vacuum
  4. customto remove pyridine
  5. filtrationThe precipitated solid was filtered
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-c6235606e28741cd93fb11a43983600b
Source dataset
uspto-grants-2015_03
Patent number
US08980911B2

Reaction notes

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