Thionyl Chloride → 3-Iodo-4-methylbenzoyl chloride

HRID 31399

Reaction equation

HRID 31399 reaction equation
S(Cl)([Cl:3])=O.[I:5][C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][C:14]=1[CH3:15])[C:9](O)=[O:10]>C(Cl)(Cl)Cl>[I:5][C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][C:14]=1[CH3:15])[C:9]([Cl:3])=[O:10]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 6216403-Iodo-4-methylbenzoic acid

Product 1

HCID 177521573-Iodo-4-methylbenzoyl chloride

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
61 °C

Procedure

Thionyl chloride (8.2 ml, 112.5 mmol) was added to a mixture of 3-iodo-4-methylbenzoic acid (18.5 g, 75 mmol) in chloroform (100 ml) and heated at 61° C. for 16 hours. The solvent was removed in vacuo and excess thionyl chloride removed by azeotroping with toluene (3×30 ml). The desired product was formed as a beige solid (19.5 g 93%) and used in subsequent reactions without further purification.

Workup

  1. customThe solvent was removed in vacuo and excess thionyl chloride
  2. customremoved
  3. customby azeotroping with toluene (3×30 ml)

Sources & evidence

ORD record
ord-f706d26ebb73471d909c51f1695ddd4a
Source dataset
uspto-grants-2008_09
Patent number
US07425555B2

Linked notes

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