ChemicalBook CAS DataBase List 1,3-PROPANEDIOL, 2-[2-(2,4-DIFLUOROPHENYL)-2-PROPEN-1-YL]-

1,3-PROPANEDIOL, 2-[2-(2,4-DIFLUOROPHENYL)-2-PROPEN-1-YL]- synthesis

5synthesis methods

Product Name:1,3-PROPANEDIOL, 2-[2-(2,4-DIFLUOROPHENYL)-2-PROPEN-1-YL]-
CAS Number:165115-73-1
Molecular formula:C12H14F2O2
Molecular Weight:228.24

2-(2,4-Difluorophenyl)-2-propenyl-propanedioic Acid Diethyl Ester

159276-62-7
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1,3-PROPANEDIOL, 2-[2-(2,4-DIFLUOROPHENYL)-2-PROPEN-1-YL]-

165115-73-1
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Yield:165115-73-1 82%

Reaction Conditions:

Stage #1:diethyl 2-[2-(2,4-difluorophenyl)-2-propen-1-yl]-1,3-propanedioate with sodium tetrahydroborate;water;lithium chloride in isopropyl alcohol at -5 - 30; for 20 h;
Stage #2: with hydrogenchloride in water;isopropyl alcohol; pH=1

Steps:

1.c
(Exl.c) Preparation oD)10.0 g of the compound of formula (CC) as oil, as obtained according to (Exl.b), were dissolved in 120 ml of isopropyl alcohol and 13.0 ml of water under stirring at 25 to 30 °C. The resulting mixture was cooled to a temperature of from 0 to -5 °C. Then, 2.3 g of lithium chloride and 2.1 g of sodium borohydride were added at 0 to -5 °C. The resulting suspension was stirred at 25 to 30 °C for 20 hours. The pH of the stirred mixture was adjusted to a value of 1 (measured by using a calibrated pH meter) by addition of 4 N aqueous HCl. Afterwards, a 20 % (w/v) aqueous solution of NaOH was added to adjust the pH to a value of 10 (measured by using a calibrated pH meter). The resulting mixture was stirred for 1 hour. Then, the lower aqueous layer was drained. From the separated organic layer, the isopropyl alcohol was distilled off, and an oil was obtained. To the oil, 100 ml of toluene and 100 ml of water were added, and the product was extracted into the toluene layer. The solvents of the resulting toluene layer were removed by distillation, under reduced pressure and the title compound was obtained as oil. The yield was 6.0 g, corresponding to a theoretical value of 82.0 %.

References:

SANDOZ AG;OBERHUBER, Michael;SALCHENEGGER, Jörg;DE SOUZA, Dominic;ALBERT, Martin;WILHELM, Thorsten;LANGNER, Martin;STURM, Hubert;SPITZENSTÄTTER, Hans-Peter WO2011/144653, 2011, A1 Location in patent:Page/Page column 57

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51336-94-8 Synthesis