2-Nitrophenol → 5-(4-nitrophenoxy)furan-2-carbaldehyde
Reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1O)([O-:3])=[O:2].Br[C:12]1[O:18][C:15]([CH:16]=[O:17])=[CH:14][CH:13]=1.C([O-])([O-])=[O:20].[K+].[K+]>CN(C=O)C>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:20][C:12]2[O:18][C:15]([CH:16]=[O:17])=[CH:14][CH:13]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
Nitrophenol (43.6 mg, 0.31 mmol) and 5-bromofurfural (50 mg, 0.28 mmol) were dissolved in dry DMF (10 ml), anhydrous K2CO3 (81 mg, 0.39 mmol) was added thereto and the resulting mixture was heated under nitrogen atmosphere at 80° C. for 5 hours. The solvent was then evaporated under reduced pressure and a mixture of water (40 ml) and ether (10 ml) was added. After separation of the phases the aqueous phase was extracted with ether (2×10 ml), the combined organic phase was dried over Na2SO4 and the organic solvents were evaporated under reduced pressure. The crude product was purified by silica gel flash chromatography to give 25 mg of pure 5-(4-nitro-phenoxy)-furan-2-carbaldehyde (38% yield).
Workup
- customThe solvent was then evaporated under reduced pressure
- additiona mixture of water (40 ml) and ether (10 ml)
- additionwas added
- customAfter separation of the phases the aqueous phase
- extractionwas extracted with ether (2×10 ml)
- dry with materialthe combined organic phase was dried over Na2SO4
- customthe organic solvents were evaporated under reduced pressure
- customThe crude product was purified by silica gel flash chromatography
Sources & evidence
- ORD record
- ord-68672f165eb442c89fd35b117e3c1d0c
- Source dataset
- uspto-grants-2010_09
- Patent number
- US07795255B2
Reaction notes
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