Methanol → Methyl 2-bromo-5-iodobenzoate
Reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:8]([I:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(Cl)(Cl)=O.[CH3:16]O>>[CH3:16][O:5][C:4](=[O:6])[C:3]1[CH:7]=[C:8]([I:11])[CH:9]=[CH:10][C:2]=1[Br:1]Participants
4
Conditions
- Temperature
- 55 °C
Procedure
To the solution of 2-bromo-5-iodo-benzoic acid (10 g, 31 mmol) in methanol (100 ml) was added thionyl chloride (5 ml, 68 mmol). The mixture was heated at 55° C. for 12 hours. The solvent and reagent were removed under reduced pressure and the mixture was diluted with EtOAc. The organic solution was washed with saturated sodium bicarbonate, water, and brine, and was dried with sodium sulfate. Concentration gave 2-bromo-5-iodo-benzoic acid methyl ester (10.5 g).
Workup
- customThe solvent and reagent were removed under reduced pressure
- additionthe mixture was diluted with EtOAc
- washThe organic solution was washed with saturated sodium bicarbonate, water, and brine
- dry with materialwas dried with sodium sulfate
- concentrationConcentration
Sources & evidence
- ORD record
- ord-f51f76b322834fa1a3fc53d7316df749
- Source dataset
- uspto-grants-2014_03
- Patent number
- US08669234B2
Reaction notes
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