Thionyl Chloride → 3-Iodo-4-methylbenzoyl chloride
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
Product 1
Reagents, catalysts & solvents 1
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
- customThe solvent was removed in vacuo and excess thionyl chloride
- customremoved
- customby azeotroping with toluene (3×30 ml)
Sources & evidence
- ORD record
- ord-f706d26ebb73471d909c51f1695ddd4a
- Source dataset
- uspto-grants-2008_09
- Patent number
- US07425555B2
Reaction notes
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