Fluorobenzene → (2-Chlor-5-iod-phenyl)-(4-fluoro-phenyl)-methanone
Reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([I:11])=[CH:7][C:3]=1[C:4]([OH:6])=O.C(Cl)(=O)C(Cl)=O.[F:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CN(C)C=O>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([I:11])=[CH:7][C:3]=1[C:4]([C:22]1[CH:23]=[CH:24][C:19]([F:18])=[CH:20][CH:21]=1)=[O:6]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 20 °C
Procedure
To a solution of 48.94 g 2-chloro-5-iodo-benzoic acid in 180 mL of fluorobenzene and 0.3 mL of N,N-dimethylformamide is added 16.2 mL of oxalyl chloride at 0 to 10° C. The solution is stirred at about 20° C. for 2 hours. The excess amount of oxalyl chloride is evaporated. The residue is diluted in 166 mL of fluorobenzene and 25.93 g of aluminum chloride is added at 0° C. in five portions. The solution is stirred at 75° C. for 1.5 hours and quenched with 300 mL of water at 0 to 25° C. The product is extracted in 300 mL of isopropylacetate and washed with two times of 200 mL brine (3 weight-%). The residue water and solvent is removed upon evaporation.
Workup
- customThe excess amount of oxalyl chloride is evaporated
- additionThe residue is diluted in 166 mL of fluorobenzene
- addition25.93 g of aluminum chloride is added at 0° C. in five portions
- stirringThe solution is stirred at 75° C. for 1.5 hours
- customquenched with 300 mL of water at 0 to 25° C
- extractionThe product is extracted in 300 mL of isopropylacetate
- washwashed with two times of 200 mL brine (3 weight-%)
- customThe residue water and solvent is removed upon evaporation
Sources & evidence
- ORD record
- ord-f18be5e303b14bd4b6eb03dbfe9e4a2a
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09127034B2
Reaction notes
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