Methyl Acrylate → 3-(2-Methyl-4-nitro-phenyl)-acrylic Acid Methyl Ester
Reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[CH3:11].CCN(C(C)C)C(C)C.[C:21]([O:25][CH3:26])(=[O:24])[CH:22]=[CH2:23].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C(#N)CC.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:26][O:25][C:21](=[O:24])[CH:22]=[CH:23][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[CH3:11]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 110 °C
Procedure
To a solution of 2-bromo-5-nitrotoluene (3.11 g, 14.39 mmol) in propionitrile (105 mL) is added DIPEA (5.1 mL, 29.28 mmol). The mixture is degassed three times. Methyl acrylate (5.2 mL, 57.74 mmol) is added and the mixture is degassed. Tri-o-tolylphosphine (1.77 g, 5.82 mmol) and Pd(OAc)2 (0.64 g, 2.85 mmol) are added and the mixture is degassed a final two times followed by heating at 110° C. for 4 h. Upon cooling, the mixture is passed through Celite and the filtrate is concentrated. The residue is partitioned between Et2O and 1N HCl. The organics are washed with saturated NaHCO3 and brine, and dried with Na2SO4. The crude material is purified by flash chromatography to yield the title compound (2.90 g, 91%).
Workup
- customThe mixture is degassed three times
- customthe mixture is degassed
- customthe mixture is degassed a final two times
- temperatureUpon cooling
- concentrationthe filtrate is concentrated
- customThe residue is partitioned between Et2O and 1N HCl
- washThe organics are washed with saturated NaHCO3 and brine
- dry with materialdried with Na2SO4
- customThe crude material is purified by flash chromatography
Sources & evidence
- ORD record
- ord-24b22d0c4ed54396b7ed52b5b6459430
- Source dataset
- uspto-grants-2006_12
- Patent number
- US07153878B2
Reaction notes
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