3-Fluorophenol → 4-(3-Fluorphenoxy)-benzonitril

반응식

C([O-])([O-])=O.[K+].[K+].Br[C:8]1[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=1.[F:16][C:17]1[CH:18]=[C:19]([OH:23])[CH:20]=[CH:21][CH:22]=1>CN(C=O)C>[F:16][C:17]1[CH:18]=[C:19]([CH:20]=[CH:21][CH:22]=1)[O:23][C:8]1[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=1

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실험 절차

A DMF (83 mL) solution of K2CO3 (12.60 g, 91.3 mmol), 4-bromobenzonitrile (15.00 g, 83.0 mmol) and 3-fluorophenol (8.2 mL, 91.3 mmol) was stirred at reflux (24 h). DMF was removed by distillation and the residue was purified by flash column chromatography on silica gel with EtOAc/hexanes (0/10 to 5195) as the eluent to obtain 4-((3′-fluoro)phenoxy)benzonitrile as a white solid (9.81 g, 56%): Rf=0.54 (EtOAc/hexanes 5/95); mp 67-69° C.; IR (nujol) 3073, 2961, 2912, 2862, 2219, 1593, 1461, 1376, 1265, 1225, 1163, 1119, 954, 869, 830, 788, 677, 543 cm−1; 1H NMR (300 MHz, CDCl3) δ 6.79 (dt, J=2.1, 9.9 Hz, 1 ArH), 6.84-6.98 (m, 2 ArH), 7.05 (d, J=9.0 Hz, 2H3), 7.32-7.41 (m, 1 ArH), 7.64 (d, J=9.0 Hz, 2H2); 13C NMR (75 MHz, CDCl3) δ 106.7 (C1), 107.9 (d, J=23.9 Hz, C2′ or C4′), 111.9 (d, J=21.1 Hz, C4′ or C2′), 115.6 (d, J=3.4 Hz, C6′), 118.5, 118.6 (CN, C3), 131.0 (d, J=9.7 Hz, C5′), 134.2 (C2), 156.2 (d, J=10.3 Hz, C1′), 160.7 (C4), 163.6 (d, J=247.1 Hz, C3′); HRMS (M+H+) (ESI+) not observed [M+H+] (calcd for C13H8FNOH+ 214.0668); Anal. Calcd. for C13H8FNO: C, 73.23; H, 3.78; F, 8.91; N, 6.57. Found: C, 73.18; H, 3.69; F, 8.68; N, 6.53.