(1,1'-Biphenyl)-2-ol → HCID 59378014, compound
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1I.C([C:14](CC)([C:18]([O-:20])=[O:19])[C:15]([O-:17])=[O:16])C.[C:23]1(C2C=CC=CC=2O)C=CC=C[CH:24]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:42]1COC[CH2:43]1>[Cu]I>[CH2:23]([O:20][C:18](=[O:19])[CH:14]([C:3]1[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]=1[Cl:1])[C:15]([O:17][CH2:42][CH3:43])=[O:16])[CH3:24]Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
To a suspension of 1-chloro-2-iodo-4-nitro-benzene (3.0 g, 10.58 mmol) in THF (11 ml) was added diethylmalonate (3.22 ml, 21.16 mmol), CuI (0.1 g, 0.529 mmol), 2-phenyl phenol (0.18 g, 1.058 mmol), and cesium carbonate (5.17 g, 15.87 mmol). The mixture was heated in a sealed tube at 70° C. for 28 hours. The mixture was cooled and partitioned between saturated aqueous ammonium chloride and EtOAc. The organic layer was separated, washed with water and brine, dried over MgSO4, filtered and concentrated to dryness under reduced pressure. Purification of the crude product by flash chromatography (hexanes:EtOAc 9:1) gave 2.3 g (688%) of 2-(2-chloro-5-nitro-phenyl)-malonic acid diethyl ester as a clear oil.
Workup
- temperatureThe mixture was cooled
- custompartitioned between saturated aqueous ammonium chloride and EtOAc
- customThe organic layer was separated
- washwashed with water and brine
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated to dryness under reduced pressure
- customPurification of the crude product by flash chromatography (hexanes:EtOAc 9:1)
Sources & evidence
- ORD record
- ord-f5043f1cc6a74beab3437a949c4348d7
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08288552B2
Reaction notes
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