Dimethyl malonate → Dimethyl 2'-methoxy-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]=[CH:21][C:20]=2[O:25][CH3:26])=[CH:15][C:14]=1[N+:27]([O-:29])=[O:28]>CS(C)=O>[CH3:26][O:25][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[C:16]1[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+:27]([O-:29])=[O:28])[CH:15]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
Dimethyl malonate (14 mL) was added dropwise to 2.9 g of sodium hydride suspended in 50 mL of dimethylsulfoxide. The mixture was stirred at 100° C. for 15 minutes and cooled to room temperature. Crude 4-fluoro-2′-methoxy-3-nitrobiphenyl in 60 mL of dimethylsulfoxide was added and the mixture stirred at 100° C. for 2 hours. The reaction mixture was cooled, quenched with 300 mL of saturated ammonium chloride solution and extracted twice with ethyl acetate. The extracts were combined, washed with saturated ammonium chloride, water, and brine, dried over anhydrous sodium sulfate and concentrated to give crude dimethyl 2′-methoxy-3-nitrobiphenyl-4-malonate as a yellow oil.
Workup
- temperaturecooled to room temperature
- stirringthe mixture stirred at 100° C. for 2 hours
- temperatureThe reaction mixture was cooled
- customquenched with 300 mL of saturated ammonium chloride solution
- extractionextracted twice with ethyl acetate
- washwashed with saturated ammonium chloride, water, and brine
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-c487a64483554e518cb59216f99d5dbc
- Source dataset
- uspto-grants-2003_03
- Patent number
- US06531502B1
Reaction notes
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