Sodium Carbonate → 5-Chloro-3-ethyl-benzofuran
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][CH:10]=[CH:11][CH3:12])=[C:4](I)[CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].C([O-])=O.[Na+].[Cl-].C([NH3+])CCC>C([O-])(=O)C.C([O-])(=O)C.[Pd+2].CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]2[O:8][CH:9]=[C:10]([CH2:11][CH3:12])[C:4]=2[CH:3]=1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 80 °C
Procedure
To a mixture of 4-chloro-2-iodo O-crotyl phenol (1.5 g, 4.86 mmol), sodium carbonate (12.2 mmol, 1.3 g), sodium formate (4.86 mmol, 330 mg), n-butyl ammonium chloride (5.34 mmol, 1.5 g) and DMF (10 mL) was added palladium di-acetate (0.24 mmol, 55 mg). The reaction was heated at 80° C. and maintained at that temperature overnight. After bringing the reaction to room temperature, the mixture was filtered. The filtrate was dried and evaporated to give a crude product, which was purified by silica gel chromatography (eluent: hexanes) to obtain 5-chloro-3-ethyl-benzofuran as a clear oil (60%, 530 mg).
Workup
- temperaturemaintained at that temperature overnight
- customthe reaction to room temperature
- filtrationthe mixture was filtered
- customThe filtrate was dried
- customevaporated
- customto give a crude product, which
- customwas purified by silica gel chromatography (eluent: hexanes)
Sources & evidence
- ORD record
- ord-2612a355020d4daa963296d6a0627058
- Source dataset
- uspto-grants-2003_06
- Patent number
- US06579879B2
Reaction notes
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