Methyl Acrylate → methyl (2E)-3-(4-fluorophenyl)prop-2-enoate
Reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][CH:3]=1.[C:9]([O:13][CH3:14])(=[O:12])[CH:10]=[CH2:11].C1(N(C)C2CCCCC2)CCCCC1>[Cl-].C([N+](CC)(CC)CC)C.CC(N(C)C)=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:8][C:5]1[CH:6]=[CH:7][C:2](/[CH:11]=[CH:10]/[C:9]([O:13][CH3:14])=[O:12])=[CH:3][CH:4]=1Participants
7
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 100 °C
Procedure
A mixture of 1-bromo-4-fluorobenzene (10 g, 57 mmol), methyl acrylate (4.5 g, 52 mmol), tetraethylammonium chloride (8.6 g, 52 mmol), N-cyclohexyl-N-methylcyclohexanamine (15 g, 78 mmol), and palladium (II) acetate (0.35 g, 1.6 mmol) in dimethylacetamide (200 mL) was heated to 100° C. under an argon atmosphere. The reaction was allowed to proceed until the aryl halide was consumed. The reaction mixture was then cooled to room temperature, diluted with Et2O, and washed three times with water. The separated organic phase was dried over MgSO4 and concentrated in vacuo. The crude product was purified by flash column chromatography on silica gel eluting with EtOAc/hexanes to afford 8.5 g (91% yield) of the title compound.
Workup
- customwas consumed
- temperatureThe reaction mixture was then cooled to room temperature
- additiondiluted with Et2O
- washwashed three times with water
- dry with materialThe separated organic phase was dried over MgSO4
- concentrationconcentrated in vacuo
- customThe crude product was purified by flash column chromatography on silica gel eluting with EtOAc/hexanes
Sources & evidence
- ORD record
- ord-c2ee950247394a87a671954feb716cc1
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09108905B2
Reaction notes
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