Water → HCID 10822693, compound
Reaction equation
Br[C:2]1[CH:9]=[C:6]([CH:7]=[O:8])[C:5]([O:10][CH3:11])=[CH:4][CH:3]=1.[S:12]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13]1.C(=O)([O-])[O-].[Na+].[Na+].O>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:11][O:10][C:5]1[CH:4]=[CH:3][C:2]([C:14]2[CH:15]=[CH:16][S:12][CH:13]=2)=[CH:9][C:6]=1[CH:7]=[O:8]Participants
Conditions
- Temperature
- 80 °C
Procedure
3 g of 5-bromo-2-anisaldehyde (0.014 mol) are dissolved in 45 ml of 1,2-dimethoxyethane and 2.68 g of 3-thiopheneboronic acid (0.021 mol) are added, followed by addition of aqueous 2N sodium carbonate solution (4.44 g, 0.042 mol) and a catalytic amount of tetrakis(triphenylphosphine)palladium (0.48 g, 4.19 10−4 mol). The reaction mixture is heated at 80° C. for 20 hours with stirring and is then cooled to room temperature and poured into water. The resulting mixture is extracted with ethyl acetate and the organic phase is washed with saturated aqueous sodium chloride solution. The resulting phase is dried over magnesium sulfate and then filtered, and the solvent is evaporated off under reduced pressure. The title product is isolated by chromatography on a column of silica (eluent: 94/6 cyclohexane/ethyl acetate). 2 g of a beige-colored solid are isolated.
Workup
- temperatureis then cooled to room temperature
- extractionThe resulting mixture is extracted with ethyl acetate
- washthe organic phase is washed with saturated aqueous sodium chloride solution
- dry with materialThe resulting phase is dried over magnesium sulfate
- filtrationfiltered
- customthe solvent is evaporated off under reduced pressure
Sources & evidence
- ORD record
- ord-3c88442379194f77bba92caaf07657cf
- Source dataset
- uspto-grants-2002_07
- Patent number
- US06417222B1
Reaction notes
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