Synthetic Route of 25893-50-9, A common heterocyclic compound, 25893-50-9, name is N-(2-Fluorophenyl)cinnamamide, molecular formula is C15H12FNO, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
General procedure: The appropriate cinnamanilide (5.0mmol), benzyl bromide (0.60mL, 5.0mmol) and KtBuO (0.55g, 5.0mmol) in THF (100mL) were stirred and heated under reflux for 1h. On cooling, the THF was removed by rotary evaporation and the residue partitioned between H2O (50mL) and EtOAc (100mL). The EtOAc was separated, washed with brine (50mL) and dried (MgSO4). Removal of the solvent gave the crude N-benzylcinnamanilide, which was either recrystallised from EtOAc/petrol, or purified by column chromatography on Al2O3, eluting with a solvent gradient from 1:1 DCM/petrol to DCM, then recrystallised as before. 4.2.10 N-Benzyl-N-(2-fluorophenyl)-3-phenylacrylamide (2k). Following the general procedure, N-(2-fluorophenyl)-3-phenylacrylamide19 1k (1.8g, 7.5mmol) was converted to 2k (2.0g, 80%) as a white solid; Rf (DCM) 0.3; mp 74-75C; deltaH (500MHz, CDCl3) 4.60 (1H, d, J 14.4Hz), 5.42 (1H, d, J 14.4Hz), 6.28 (1H, d, J 15.4Hz), 6.98 (1H, dt, J 1.5, 7.7Hz), 7.09 (1H, dt, J 0.7, 8.0Hz), 7.16 (1H, ddd, J 1.3, 7.7, 8.0Hz), 7.2-7.39 (11H, m), 7.78 (1H, d, J 15.4Hz); deltaC (CDCl3) 52.33 (CH2), 116.90 (CH, d, J 20Hz), 117.9 (CH), 124.7 (CH, d, J 4Hz), 127.5 (CH), 128.0 (CH), 128.4 (CH), 128.8 (CH), 129.0 (CH), 129.3 (C, d, J 13Hz), 129.8 (CH), 130.0 (CH, d, J 8Hz), 131.1 (CH), 135.1 (C), 137.1 (C), 143.2 (CH), 158.3 (C, d, J 250Hz), 166.2 (C); numax (solid) 1651, 1614, 1606, 1496, 1387, 1330, 1226, 1215, 1191, 1107, 1079, 980, 861, 818, 763, 733, 699, 679cm-1; m/z (EI) 331 (34, M+), 201 (38), 131 (100), 103 (36), 91 (20%); HMRS (EI) M+, found 331.1365. C22H18FNO requires 331.1367.
The synthetic route of 25893-50-9 has been constantly updated, and we look forward to future research findings.
Reference:
Article; King, Frank D.; Caddick, Stephen; Tetrahedron; vol. 69; 40; (2013); p. 8592 – 8601;,
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