Dimethylformamide → Methyl 5-chloro-2-iodobenzoate
Reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([I:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].O=S(Cl)Cl.[CH3:16]N(C=O)C>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([I:11])=[C:6]([CH:10]=1)[C:7]([O:9][CH3:16])=[O:8]Participants
4
Conditions
- Temperature
- 23 °C
Procedure
A solution of 5-chloro-2-iodobenzoic acid (3.0 g, 10.62 mmol), SOCl2 (12 mL) and DMF (0.6 mL) was gently warmed with a heat gun until the mixture became homogeneous (15 min). The solution was maintained at 23° C. for additional 30 min and then the solution was concentrated. MeOH (24 mL) was added to the crude residue and the solution was maintained at 23° C. for 30 min. The solution was concentrated and the residue was purified by flash chromatography on Biotage silica gel cartridge (cyclohexane to cyclohexane:EtOAc=85:15) to afford methyl 5-chloro-2-iodobenzoate (3.02 g, 10.20 mmol, 96%).
Workup
- custom(15 min)
- concentrationthe solution was concentrated
- additionMeOH (24 mL) was added to the crude residue
- temperaturethe solution was maintained at 23° C. for 30 min
- concentrationThe solution was concentrated
- customthe residue was purified by flash chromatography on Biotage silica gel cartridge (cyclohexane to cyclohexane:EtOAc=85:15)
Sources & evidence
- ORD record
- ord-1d32bbfc85e54b1e897fd3db73d02f11
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09321776B2
Reaction notes
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