Dimethyl malonate → Dimethyl 3'-ethoxy-3-nitrobiphenyl-4-malonate
Reaction equation
[C:1]([O:8][CH3:9])(=[O:7])[CH2:2][C:3]([O:5][CH3:6])=[O:4].[H-].[Na+].F[C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH2:26][CH3:27])[CH:20]=2)=[CH:15][C:14]=1[N+:28]([O-:30])=[O:29]>CS(C)=O>[CH2:26]([O:25][C:21]1[CH:20]=[C:19]([C:16]2[CH:17]=[CH:18][C:13]([CH:2]([C:1]([O:8][CH3:9])=[O:7])[C:3]([O:5][CH3:6])=[O:4])=[C:14]([N+:28]([O-:30])=[O:29])[CH:15]=2)[CH:24]=[CH:23][CH:22]=1)[CH3:27]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
Dimethyl malonate (11.4 ml) was added dropwise to 4.0 g of sodium hydride suspended in 20 ml of dimethylsulfoxide. The mixture was heated to 100° C. for 10 minutes and cooled to room temperature. Crude 4-fluoro-3′-ethoxy-3-nitrobiphenyl (5.3 g) in 25 ml of dimethylsulfoxide was added and the mixture was stirred at 100° C. for 2 hours. The reaction mixture was cooled and quenched with 300 ml of saturated ammonium chloride solution and extracted three times with ethyl acetate. The extracts were combined, washed with water and brine, dried over anhydrous sodium sulfate and concentrated to give crude dimethyl 3′-ethoxy-3-nitrobiphenyl-4-malonate as a yellow oil.
Workup
- temperaturecooled to room temperature
- temperatureThe reaction mixture was cooled
- customquenched with 300 ml of saturated ammonium chloride solution
- extractionextracted three times with ethyl acetate
- washwashed with water and brine
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-fccbc79a4c294cbe81b72d74c55cb386
- Source dataset
- uspto-grants-2003_03
- Patent number
- US06531502B1
Reaction notes
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