Benzene, 1,2-dichloro-4-iodo- → 3-(3,4-Dichlorophenyl)propanal
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][C:3]=1[Cl:9].[CH:10]([OH:13])=[CH:11][CH3:12].C([O-])(O)=O.[Na+]>CN(C=O)C.[N+](CCCC)(CCCC)(CCCC)CCCC.[Cl-].CC([O-])=O.CC([O-])=O.[Pd+2]>[Cl:9][C:3]1[CH:4]=[C:5]([CH2:12][CH2:11][CH:10]=[O:13])[CH:6]=[CH:7][C:2]=1[Cl:1]Participants
7
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 50 °C
Procedure
To a solution of 1,2-dichloro-4-iodobenzene (5.44 g, 20 mmol) in DMF (60 ml) was added Bu4NCl (5.56 g, 20 mmol), propenol (4.64 g, 80 mmol), Pd(OAc)2 (224 mg, 1 mmol) and NaHCO3 (10.0 g, 120 mmol) successively at room temperature. The mixture was heated at 50° C. for 12 hour. After cooling to the room temperature, the mixture was poured into ice-water, extracted with DCM three times. The combined organic layers were washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography using PE/EA (20/1) as eluent to afford the title compound (2.01 g, yield 49.8%).
Workup
- temperatureAfter cooling to the room temperature
- extractionextracted with DCM three times
- washThe combined organic layers were washed with brine
- dry with materialdried over Na2SO4
- concentrationconcentrated under reduced pressure
- customThe residue was purified by column chromatography
Sources & evidence
- ORD record
- ord-46f948d4cafa4b82864e6dd87d3cfd78
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08431581B2
Reaction notes
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