Sulfuric Acid → Diethyl (3-chloro-2,4-difluorobenzoyl)malonate

HRID 2209982

Reaction equation

[Mg].[C:2]([O:10][CH2:11][CH3:12])(=[O:9])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[Cl:13][C:14]1[C:15]([F:24])=[C:16]([CH:20]=[CH:21][C:22]=1[F:23])[C:17](Cl)=[O:18].S(=O)(=O)(O)O>C(O)C.C1(C)C=CC=CC=1.C(Cl)(Cl)(Cl)Cl>[Cl:13][C:14]1[C:15]([F:24])=[C:16]([CH:20]=[CH:21][C:22]=1[F:23])[C:17]([CH:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[C:2]([O:10][CH2:11][CH3:12])=[O:9])=[O:18]

Participants

Conditions

Temperature: 60 °C

Procedure

3.9 g (0.16 mol) of magnesium are introduced into 8.6 ml of ethanol, and the reaction is started up using carbon tetrachloride. A solution of 23.1 g (0.144 mol) of diethyl malonate in 16.3 ml of ethanol is added dropwise at an internal temperature of 50°-60° C. in such a manner that the temperature is maintained. The mixture is subsequently stirred for one hour at 60° C. A solution of 31.3 g (0.148 mol) of 3-chloro-2,4-difluorobenzoyl chloride in 16 ml of toluene is then added dropwise at -10° to -5° C., and stirring is continued for one hour at 0° C. and subsequently overnight while the mixture comes to room temperature. The reaction mixture is poured into ice-water, acidified using 10 ml of concentrated sulphuric acid and extracted using toluene. The toluene phase is washed using saturated sodium chloride solution, and the solvent is removed in vacuo.

Workup

temperatureis maintained
stirringstirring
waitis continued for one hour at 0° C. and subsequently overnight while the mixture
customcomes to room temperature
extractionextracted
washThe toluene phase is washed
customthe solvent is removed in vacuo

Sources & evidence

ORD record: ord-5ed51ee65e9d41f5ad9b0827b8619d48
Source dataset: uspto-grants-1995_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05457104

Linked notes

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