Thionyl Chloride → 2,6-Dichloro-4-iodobenzoyl chloride

HRID 2366217Notes

Reaction equation

HRID 2366217 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([I:11])[CH:8]=[C:7]([Cl:12])[C:3]=1[C:4](O)=[O:5].S(Cl)([Cl:15])=O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:10]=[C:9]([I:11])[CH:8]=[C:7]([Cl:12])[C:3]=1[C:4]([Cl:15])=[O:5]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 513418772,6-Dichloro-4-iodobenzoic acid

Product 1

HCID 866489582,6-Dichloro-4-iodobenzoyl chlorideYield 99%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 2,6-dichloro-4-iodobenzoic acid (5.50 g, 17.4 mmol) in thionyl chloride (52 mL) was heated under reflux for 2 hours then diluted with toluene and concentrated under reduced pressure. The resultant residue was partitioned between EtOAc and saturated aqueous sodium bicarbonate solution. The organic layer was dried over Na2SO4 and concentrated under reduced pressure to give the desired compound as a yellow oil (5.75 g, 99% yield). 1H NMR (400 MHz, CDCl3) δ 7.75 (s, 2H).

Workup

  1. temperatureunder reflux for 2 hours
  2. concentrationconcentrated under reduced pressure
  3. customThe resultant residue was partitioned between EtOAc and saturated aqueous sodium bicarbonate solution
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c136f3c39283497a82de3e10f43af110
Source dataset
uspto-grants-2014_04
Patent number
US08697708B2

Reaction notes

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