Water → 2-Hydroxy-5-(thiophen-3-yl)benzaldehyde
Reaction equation
Br[C:2]1[CH:9]=[C:6]([CH:7]=[O:8])[C:5]([OH:10])=[CH:4][CH:3]=1.[S:11]1[CH:15]=[CH:14][C:13](B(O)O)=[CH:12]1.[F-].[Cs+].O>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.COCCOC.CO>[OH:10][C:5]1[CH:4]=[CH:3][C:2]([C:13]2[CH:14]=[CH:15][S:11][CH:12]=2)=[CH:9][C:6]=1[CH:7]=[O:8]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 80 °C
Procedure
0.15 g of tetrakis(triphenylphosphine)palladium catalyst (1.3 10−4 mol) is added to a solution of 5-bromosalicylaldehyde (0.86 g, 0.0043 mol) and of 3-thiopheneboronic acid (0.6 g, 0.0047 mol) in 10 ml of 1,2-dimethoxyethane and 5 ml of methanol. 1.3 g of cesium fluoride are added and the mixture is heated at 80° C. for 20 hours. The reaction mixture is cooled to room temperature and poured into water. The resulting mixture is extracted with dichloromethane and the organic phase is washed with saturated aqueous sodium chloride solution. The organic phase is dried over magnesium sulfate, filtered and concentrated under reduced pressure. The title product is isolated by chromatography on a column of silica (eluent: 88/12 cyclohexane/ethyl acetate. 0.62 g of a pale yellow solid is recovered.
Workup
- temperatureThe reaction mixture is cooled to room temperature
- extractionThe resulting mixture is extracted with dichloromethane
- washthe organic phase is washed with saturated aqueous sodium chloride solution
- dry with materialThe organic phase is dried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-a181cd352cf147818d2ec63bbeb70432
- Source dataset
- uspto-grants-2002_07
- Patent number
- US06417222B1
Reaction notes
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