Diethyl (ethoxymethylene)malonate → Diethyl 2-((4-bromophenylamino)methylene)malonate
Reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.C(O[CH:12]=[C:13]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:14]([O:16][CH2:17][CH3:18])=[O:15])C.CCCC(C)C>C1(C)C=CC=CC=1>[CH2:17]([O:16][C:14](=[O:15])[C:13](=[CH:12][NH:6][C:5]1[CH:7]=[CH:8][C:2]([Br:1])=[CH:3][CH:4]=1)[C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH3:18]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 150 °C
Procedure
A 20 mL microwave vial was charged with 4-bromoaniline (6.881 g, 40.0 mmol), diethyl ethoxymethylenemalonate (8.650 g, 40.0 mmol) and toluene (5 mL). The vial was capped and the mixture was microwave heated at 150° C. for 30 min. After cooling, the solution was poured onto 50 mL of vigorously stirred iso-hexane. A thick, white precipitate formed and the suspension was stirred for another 15 min. The suspension was filtered and the product washed with 20 mL of iso-hexane. The product was dried under vacuum to give 11.678 g (85%) of 2-[(4-bromo-phenylamino)methylene]malonic acid diethyl ester. MS (EST+) m/z 342, 344 (MH+).
Workup
- customThe vial was capped
- temperatureAfter cooling
- customA thick, white precipitate formed
- filtrationThe suspension was filtered
- washthe product washed with 20 mL of iso-hexane
- customThe product was dried under vacuum
Sources & evidence
- ORD record
- ord-02a6b284f333496c91aeb5bfdeb6c7a9
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08957092B2
Reaction notes
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