Hydrochloric Acid → Diethyl (3-difluoromethoxy-2,4,5-trifluoro-6-nitrobenzoyl)malonate
Reaction equation
[F:1][CH:2]([F:19])[O:3][C:4]1[C:5]([F:18])=[C:6]([C:10]([N+:15]([O-:17])=[O:16])=[C:11]([F:14])[C:12]=1[F:13])[C:7](Cl)=[O:8].[C:20]([O-:26])(=[O:25])[CH2:21][C:22]([O-:24])=[O:23].[CH2:27](C(CC)(O[Mg+2])C)[CH3:28].Cl.[CH2:36](OCC)[CH3:37]>>[F:1][CH:2]([F:19])[O:3][C:4]1[C:5]([F:18])=[C:6]([C:10]([N+:15]([O-:17])=[O:16])=[C:11]([F:14])[C:12]=1[F:13])[C:7]([CH:21]([C:20]([O:26][CH2:36][CH3:37])=[O:25])[C:22]([O:24][CH2:27][CH3:28])=[O:23])=[O:8]Participants
Procedure
The whole of the 3-difluoromethoxy-2,4,5-trifluoro-6-nitrobenzoyl chloride [(XIII), R1 =--OCHF2, R3' =NO2, X=X'=F] prepared as described above was dissolved in 150 ml of anhydrous diethyl ether, and this solution was added dropwise, with stirring at room temperature, to the suspension of diethyl ethoxymagnesium malonate. The resulting mixture was then stirred at room temperature for an additional 2 hours. At the end of this time, 100 ml of 1N aqueous hydrochloric acid were added to the reaction mixture, and, after the mixture had been vigorously stirred, the organic layer was separated, washed with water and dried over anhydrous sodium sulfate. The solvent was then removed by evaporation under reduced pressure to give 31.2 g of diethyl (3-difluoromethoxy-2,4,5-trifluoro-6-nitrobenzoyl)malonate [(XIV), R1 =--OCHF2, R3' =NO2, R17 =C2H5, X=X'=F] as a red liquid.
Workup
- additionthis solution was added dropwise
- stirringafter the mixture had been vigorously stirred
- customthe organic layer was separated
- washwashed with water
- dry with materialdried over anhydrous sodium sulfate
- customThe solvent was then removed by evaporation under reduced pressure
Sources & evidence
- ORD record
- ord-f13a89b19c454a10a14283d812fe9d6b
- Source dataset
- uspto-grants-1996_03
- Patent number
- US05496951
Reaction notes
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