Butyl Acrylate → HCID 66733998, compound
Reaction equation
Br[C:2]1[CH:3]=[C:4]([F:10])[C:5]([CH3:9])=[C:6]([F:8])[CH:7]=1.[C:11]([O:15][CH2:16][CH2:17][CH2:18][CH3:19])(=[O:14])[CH:12]=[CH2:13].C1N2CCN(CC2)C1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CCOCC>[CH2:16]([O:15][C:11](=[O:14])[CH:12]=[CH:13][C:2]1[CH:3]=[C:4]([F:10])[C:5]([CH3:9])=[C:6]([F:8])[CH:7]=1)[CH2:17][CH2:18][CH3:19]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 120 °C
Procedure
To a solution of 5-bromo-1,3-difluoro-2-methyl-benzene (6.910 g; 33.379 mmol) in anhydrous DMF (200 ml) were added successively butyl acrylate (7.15 ml; 50.062 mmol), DABCO (157 mg; 1.333 mmol), potassium carbonate (4.612 g; 33.379 mmol), and palladium acetate (150 mg; 0.669 mmol). The resulting brown suspension was heated to 120° C. for 1 h. The reaction mixture was allowed to cool to rt before ether (400 ml) was added. This mixture was then washed with water (2×200 ml), and the mixed aq. layers were further extracted with ether (150 ml). The combined organic layers were dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Purification by FC (DCM/heptane=1/1=>DCM) gave the pure product 3-(3,5-difluoro-4-methyl-phenyl)-acrylic acid butyl ester as a yellow oil which was further dried under HV (4.690 g; 55%). LC-MS: tR=1.10 min.; [M+H]+: no ionisation.
Workup
- additionwas added
- washThis mixture was then washed with water (2×200 ml)
- extractionthe mixed aq. layers were further extracted with ether (150 ml)
- dry with materialThe combined organic layers were dried over anh. MgSO4
- filtrationfiltered
- concentrationconcentrated to dryness under reduced pressure
- customPurification by FC (DCM/heptane=1/1=>DCM)
Sources & evidence
- ORD record
- ord-482cf023f68c476b9ff7401d21f78deb
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08188082B2
Reaction notes
Loading…