Hydrochloric Acid → Methyl 3-bromo-5-iodobenzoate
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([I:11])[CH:10]=1)[C:5]([OH:7])=[O:6].Cl.Cl[CH2:14]Cl>CO>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([I:11])[CH:10]=1)[C:5]([O:7][CH3:14])=[O:6]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
To a suspension of 3-bromo-5-iodobenzoic acid (993 g, 3.04 mol) in methanol (6.0 L) was added hydrochloric acid (37%; 20.0 mL, 244 mmol). The mixture was heated to 70° C. After 72 h, the mixture was cooled to ambient temperature. Dichloromethane (2.5 L) was added and the mixture was partially concentrated. The suspension was filtered and the filtered cake was washed with cold methanol to give the title compound as a white solid (846 g).
Workup
- temperaturethe mixture was cooled to ambient temperature
- concentrationthe mixture was partially concentrated
- filtrationThe suspension was filtered
- washthe filtered cake was washed with cold methanol
Sources & evidence
- ORD record
- ord-096e8577f0fa4749966ed02cc394852a
- Source dataset
- uspto-grants-2012_08
- Patent number
- US08247401B2
Reaction notes
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