4-Fluorobenzonitrile → HCID 21880817, compound

Participants

Reaction Conditions

Reaction Steps

2,6-Diallylphenol (3.8 gm, 0.02 mol) was oxidized with m-chloroperbenzoic acid as described in Example 1 to give 2,6-di(2,3-epoxypropyl)phenol. MS m/z 206 (M+ calcd for C12H14O3=206). H NMR (300 MHz, CDCl3) d 2.65 (d, 2, CH2 epoxypropyl) 2.75–2.96 (CH2 epoxypropyl), 3.12 (d, 2, CH epoxypropyl), 3.25–3.35(m, 2, CH epoxypropyl), 6.80 (t, 1, aromatic), 7.10 (d, 2, aromatic). The product 2,6-di(2,3-epoxypropyl)phenol was diluted with dimethylacetamide (50 ml) and neutralized with sodium hydroxide. 4-Fluorobenzonitrile (1 equivalent of the phenol) was added and the mixture heated and stirred overnight at 50° C. After cooling, the reaction was diluted with ethyl acetate and washed with water (4×), dried over MgSO4 and evaporated to give 2,6-di(2,3epoxypropyl)phenyl 4-cyanophenyl ether. MS m/z 307 (M+ calcd for C19H17O3N=307). H NMR (300 MHz, CDCl3) d 2.50, (d, 2, CH2 epoxypropyl CH2), 2.65–2.90 (m, 4, CH2 epoxypropyl), 3.15–3.30 (m, 2, CH2 epoxypropyl), 3.45–3.75 (m, 2, epoxypropyl CH), 6.75–7.06 (m, 3, aromatic), 7.00–7.75 (m, 4, aromatic).

Provenance & Evidence