Sodium Iodide → Ethyl 4-(cyclohexylmethyloxy)-3-nitrobenzoate
Reaction equation
[OH:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]=1[N+:13]([O-:15])=[O:14].C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[Na+].[CH:24]1([CH2:30]Br)[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1>CN(C=O)C>[CH:24]1([CH2:30][O:1][C:2]2[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]=2[N+:13]([O-:15])=[O:14])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1Participants
6
Conditions
- Temperature
- 60 °C
Procedure
To a mixture of ethyl 4-hydroxy-3-nitrobenzoate (2-1) (2.11g, 10.0 mmol), cesium carbonate (6.52 g, 20.0 mmol), and sodium iodide (0.15g, 1.0 mmol) in DMF (20 ml) under nitrogen was added cyclohexylmethylbromide (1.67 ml, 12.0 mmol). The mixture was stirred 48 h at 60° C. The resulting mixture was evaporated under reduced pressure. To the residue was added water (100 ml), and the aqueous mixture was extracted with methylene chloride (2×200 ml). The organic fraction was washed with saturated sodium carbonate solution (100 ml) and brine (100 ml), dried (sodium sulfate), and the solvent was evaporated under reduced pressure. The residue was crystallized from ether/hexane to give product 21-2 as yellow crystals, mp: 79°-80° C.
Workup
- customThe resulting mixture was evaporated under reduced pressure
- additionTo the residue was added water (100 ml)
- extractionthe aqueous mixture was extracted with methylene chloride (2×200 ml)
- washThe organic fraction was washed with saturated sodium carbonate solution (100 ml) and brine (100 ml)
- dry with materialdried (sodium sulfate)
- customthe solvent was evaporated under reduced pressure
- customThe residue was crystallized from ether/hexane
Sources & evidence
- ORD record
- ord-40c8a642c40a4d21a01d504f769bc9f9
- Source dataset
- uspto-grants-1999_02
- Patent number
- US05872138
Reaction notes
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