Benzenepropanoic acid, 2,4-dichloro-α-[(dimethylamino)methylene]-5-fluoro-β-oxo-, ethyl ester synthesis
- Product Name:Benzenepropanoic acid, 2,4-dichloro-α-[(dimethylamino)methylene]-5-fluoro-β-oxo-, ethyl ester
- CAS Number:105392-20-9
- Molecular formula:C14H14Cl2FNO3
- Molecular Weight:334.17
1117-37-9
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Yield:105392-20-9 69%
Reaction Conditions:
with N-ethyl-N,N-diisopropylamine at 20 - 90; for 3.33333 h;
Steps:
3.a
Ethyl 2- (2, 4-dichloro-5-lluorobenzoyl)-3- (dimethylamino) acrylate. A mixture of ethyl 3,3-dimethylaminoacrylate (3.10 g, 21.6 mmol) and N, N-diisopropylethylamine (8.0 mL, 5.94 g, 45.9 mmol) was stirred at rt and a solution of 2, 4-dichloro-5- fluorobenzoyl chloride (4.92 g, 21. 6 mmol) was added drop-wise via addition funnel over 20 m. The cloudy yellow solution that formed was placed in an oil bath at 85-90 °C. After 3 h, the mixture that formed was filtered and the solid was washed with benzene. The dark filtrate was concentrated and the residue was triturated with hexanes (50 mL). The solid that didn't dissolve was collected and washed with hexanes (20 mL). The resulting solid was partitioned between water and EtOAc. The EtOAc layer was washed with water (3 x 25 mL), brine, dried (Na2SO4), filtered and concentrated to 5.0 g (69%) of the desired compound
References:
WO2003/97564,2003,A2 Location in patent:Page/Page column 23
86522-89-6
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