2-Fluoro-1-(2-fluoro-phenyl)-ethanone synthesis
- Product Name:2-Fluoro-1-(2-fluoro-phenyl)-ethanone
- CAS Number:1402412-84-3
- Molecular formula:C8H6F2O
- Molecular Weight:156.13
218771-68-7
1402412-84-3
The general procedure for the synthesis of 2-fluoro-1-(2-fluorophenyl)ethanone from 1-(2-fluorophenyl)-2-hydroxyacetophenone was as follows: 1-(2-fluorophenyl)-2-hydroxyacetophenone [CAS 218771-68-7] (2.77 g, 18.0 mmol) was dissolved in dichloromethane (42 ml), and triethylamine (6.36 g, 62.8 mmol), triethylamine trihydrofluoride (3.05 g, 18.0 mmol) and n-butyl ninafluoroacetylsulfonyl fluoride (8.48 g, 26.9 mmol) were added sequentially at 0 °C. The reaction tube was sealed and the reaction mixture was stirred at room temperature overnight. After completion of the reaction, the dark red solution was poured into a mixture of saturated sodium bicarbonate solution and ice and extracted with dichloromethane. The organic layer was separated, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product was purified by rapid chromatography on silica gel (Telos Flash Silica) using dichloromethane as eluent to afford 2-fluoro-1-(2-fluorophenyl)ethanone (1.23 g, 61% yield) as a yellow semi-solid.
445-27-2
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1402412-84-3
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Yield:1402412-84-3 89%
Reaction Conditions:
Stage #1: 2'-Fluoroacetophenonewith lithium hexamethyldisilazane in tetrahydrofuran at -74; for 0.666667 h;
Stage #2: with chloro-trimethyl-silane in tetrahydrofuran at -74 - 20;
Stage #3: with Selectfluor in acetonitrile at 4 - 20; for 10.5 h;
References:
Fuchino, Kouki;Mitsuoka, Yasunori;Masui, Moriyasu;Kurose, Noriyuki;Yoshida, Shuhei;Komano, Kazuo;Yamamoto, Takahiko;Ogawa, Masayoshi;Unemura, Chie;Hosono, Motoko;Ito, Hisanori;Sakaguchi, Gaku;Ando, Shigeru;Ohnishi, Shuichi;Kido, Yasuto;Fukushima, Tamio;Miyajima, Hirofumi;Hiroyama, Shuichi;Koyabu, Kiyotaka;Dhuyvetter, Deborah;Borghys, Herman;Gijsen, Harrie J.M.;Yamano, Yoshinori;Iso, Yasuyoshi;Kusakabe, Ken-Ichi [Journal of Medicinal Chemistry,2018,vol. 61,# 12,p. 5122 - 5137] Location in patent:supporting information
218771-68-7
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1402412-84-3
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375-72-4
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1402412-84-3
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$30.00/100mg