Methyl 2-(4-cyano-3-fluorophenyl)acetate synthesis
- Product Name:Methyl 2-(4-cyano-3-fluorophenyl)acetate
- CAS Number:444807-50-5
- Molecular formula:C10H8FNO2
- Molecular Weight:193.17
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Yield:444807-50-5 60.2%
Reaction Conditions:
with tetrakis(triphenylphosphine) palladium(0) in N,N-dimethyl-formamide at 155; for 1.5 h;Inert atmosphere;Microwave irradiation;
Steps:
35.2 Step 2: methyl 4-cyano-3-fluorophenylacetate
Ethyl-4-bromo-3-fluorophenylacetate (1.3 g, 5.3 mmol), zinc cyanide (924 mg, 7.89 mmol) and N,N-dimethylformamide (10 mL) were added to a 20 mL microwave tube. The mixture was nitrogen sparged for 5 min, tetrakis(triphenylphosphine)palladium (613 mg, 0.53 mmol) was added, and the mixture was stirred and heated to 155 °C for 1.5 hours under microwave. After completion of reaction, the mixture was cooled to room temperature, and extracted with ethyl acetate for three times, and the organic layers were combined, washed 5 times with water, and finally washed with saturated sodium chloride, and the organic layer was concentrated in vacuo to get a crude product. Then the crude product was separated by a silica gel column (petroleum ether: ethyl acetate = 8:1-5:1) to give the product (while solid, 620 mg), with a yield of 60.2%. 1H NMR(400 MHz, CDCl3) 7.58 (t, J= 7.2 Hz, 1H), 7.18 (d, J= 8.7 Hz, 2H), 3.72 (s, 3H), 3.69 (s, 2H). MS (ESI) m/z: 194.1(MH+)
References:
EP3476829,2019,A1 Location in patent:Paragraph 0216
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