3-Fluorophenol → HCID 28368207, compound

Participants

Reaction Steps

A mixture of 4-(bromomethyl)benzonitrile (23.50 g, 120.0 mmol), K2CO3 (55.20 g, 400.0 mmol) and 3-fluorophenol (11.21 g, 100.0 mmol) were heated at reflux in acetone (400 mL) (16 h). The volatiles were evaporated and the residue was diluted with CH2Cl2 (300 mL). The organic layer was washed with H2O (300 mL), dried (MgSO4) and concentrated in vacuo to give white needles (19.81 g, 87%): Rf=0.40 (9/1 hexanes/ethyl acetate); mp 69-70° C.; 1H NMR (CDCl3) δ 5.02 (s, CH2O), 6.56-6.67 (m, 3 ArH), 7.16 (q, J=7.7 Hz, 1 ArH), 7.45 (d, J=7.1 Hz, 2 ArH), 7.59 (d, J=8.1 Hz, 2 ArH); 13C NMR (CDCl3) δ 60.1 (CH2O), 102.8 (d, J=24.4 Hz, C2′ or C4′), 108.3 (d, J=21.1 Hz, C4′ or C2′), 110.4 (d, J=2.8 Hz, C6′), 111.9 (Are), 118.6 (CN), 127.5 (ArC), 130.4 (d, J=9.7 Hz, C5′), 132.4, 141.9 (2 Are), 159.4 (d, J=10.8 Hz, C1′), 163.6 (d, J=244.2 Hz, C3′); LRMS (M+Na+) (ESI+) 250.0 [M+Na+] (calcd for C14H10NONa+ 250.0).

Provenance & Evidence