2-Propenoic acid, 2-fluoro-3-(4-methoxyphenyl)-, (2Z)- synthesis

7synthesis methods

Product Name:2-Propenoic acid, 2-fluoro-3-(4-methoxyphenyl)-, (2Z)-
CAS Number:26928-12-1
Molecular formula:C10H9FO3
Molecular Weight:196.18

2356-16-3 Synthesis

2356-16-3
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123-11-5 Synthesis

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2-Propenoic acid, 2-fluoro-3-(4-methoxyphenyl)-, (2Z)-

26928-12-1
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Yield: 65%

Reaction Conditions:

Stage #1:ethyl(diethylphosphono)(fluoro)acetate;4-methoxy-benzaldehyde with 1,8-diazabicyclo[5.4.0]undec-7-ene in tetrahydrofuran at 10 - 20; for 21 h;Large scale;
Stage #2: with sodium hydroxide in tetrahydrofuran;ethanol;water at 20; for 2 h;Large scale;

Steps:

1 Example 1
To a solution of the compound (13) (65.0 kg) in tetrahydrofuran (108.0 kg) were added diazabicycloundecene (40.8 kg) and tetrahydrofuran (13.4 kg) while stirring the solution at room temperature. The compound (12) (30.4 kg) and tetrahydrofuran (13.4 kg) were added thereto at 10°C., the reaction mixture was then stirred at room temperature for 21 hours. Ethanol (119.8 kg) and 7.4% aqueous sodium hydroxide solution (358.2 kg) were added thereto at room temperature, and the mixture was stirred for 2 hours. Water (137.7 kg), 35% hydrochloric acid (69.0 kg) and water (15.2 kg) were added thereto in that order at room temperature, and the mixture was stirred at room temperature for 30 minutes and at 0°C. for 1 hour. The crystals were collected by filtration, and washed with a mixed solution of ethanol (24.0 kg) and water (60.9 kg), and further with water (151.9 kg). The crystals were dried at 60°C. or less to obtain the compound ( 14) (28.6 kg) (yield 65%). MS (ESI): m/z 195.1 [M-H]-

References:

MITSUBISHI TANABE PHARMA CORPORATION;TSURUMOTO, Joji;MOROKUMA, Kenji US2020/239440, 2020, A1 Location in patent:Paragraph 0097-0098