Methyl Acrylate → Methyl (E)-3-(3,5-dichlorophenyl)acrylate
Reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](I)[CH:5]=[C:4]([Cl:9])[CH:3]=1.[C:10]([O:14][CH3:15])(=[O:13])[CH:11]=[CH2:12].C(N(CC)CC)C>CN(C=O)C.CCOC(C)=O>[Cl:1][C:2]1[CH:7]=[C:6](/[CH:12]=[CH:11]/[C:10]([O:14][CH3:15])=[O:13])[CH:5]=[C:4]([Cl:9])[CH:3]=1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 80 °C
Procedure
To 1,3-dichloro-5-iodobenzene (300 mg, 1.099 mmol) and methyl acrylate (0.099 ml, 1.099 mmol) in DMF (10 ml) under nitrogen was added [Pd(t-BuP)]2 (56.1 mg, 0.110 mmol) and triethylamine (0.306 ml, 2.199 mmol). The reaction mixture was heated to 80° C. for 2 h. The reaction mixture was diluted with EtOAc and filtered through a silica cartridge (2 g). The organic solution was washed with water, saturated sodium bicarbonate solution, water and brine. The organic portion was dried using a phase separating column and the solvent was removed under reduced pressure to afford the title compound;
Workup
- filtrationfiltered through a silica cartridge (2 g)
- washThe organic solution was washed with water, saturated sodium bicarbonate solution, water and brine
- customThe organic portion was dried
- customseparating column
- customthe solvent was removed under reduced pressure
Sources & evidence
- ORD record
- ord-c4cd2e1bef2c4beeb6d60d95b85fd10c
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09409895B2
Reaction notes
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