Related Products of 60144-53-8, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 60144-53-8, name is tert-Butyl (4-fluorophenyl)carbamate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.
(4-Fluoro-phenyl)-carbamic acid terf-butyl ester (2.1 1 g, 10.0 mmol, ABCR, Karlsruhe, Germany) was added to a round bottom and purged with nitrogen. Anhydrous tetrhydrofuran (200 mL) was added to dissolve the solids and the flask placed in a dry ice / acetone bath (internal temperature -74 C uncorrected). terf-Butyl lithium (1 .7 M in pentane, 14.2 mL, 24.0 mmol) was added over 5 min causing a yellow color to develop. After the addition was complete the reaction was stirred in a -20 C bath for 1 h. At this point, 3-ethoxymethacrolein (1.43 mL, 12.0 mmol) was added dropwise over 5 min, keeping the temperature below -19 C. The reaction was stirred at -20 C for 2 h before slowly adding trifluoroacetic acid (14 mL) over 5 min. The red solution was stirred at room temperature for 16 h before bring to pH 12 with 1 N NaOH. This was extracted twice with ethyl acetate and the combined organics dried over MgS04. Purification by silica gel flash chromatography (ethyle acetate / heptanes) gave impure desired material. This was extracted into three portions of 1 N HCI, the combined aqueous layers were brought to pH 12 with 6 N NaOH, and then extracted into two portions of ethyl acetate. The combined organics were dried over MgS04 and concentrated in vacuo to give 6-fluoro-3-methyl-quinoline (48.0 mg) as an orange oil. 1 H NMR (400 MHz, CDCI3) delta 8.74 (s, 1 H) 8.07 (dd, J=9.1 , 5.4 Hz, 1 H) 7.88 (s, 1 H) 7.33 – 7.46 (m, 2 H) 2.53 (s, 3 H); MS (M+1 ): 162.1 .
The synthetic route of tert-Butyl (4-fluorophenyl)carbamate has been constantly updated, and we look forward to future research findings.
Reference:
Patent; PFIZER INC.; DIDIUK, Mary; FILIPSKI, Kevin J.; GUZMAN-PEREZ, Angel; LEE, Esther C.; PFEFFERKORN, Jeffrey A.; STEVENS, Benjamin; TU, Meihua; WO2013/14569; (2013); A1;,
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