Acrylonitrile → 3-{[6-(2,4-Difluorophenyl)-2-naphthyl]thio}propanenitrile

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-(2,4-difluorophenyl)-2-naphthyl hydrosulfide (prepared from 6-bromo-2-naphthol according to the methods of Example 1 Steps 1 and 2 and Example 2 Step 2, 7.3 g, 24.7 mmol), acrylonitrile (2.6 mL, 39.5 mmol) and triethylamine (370 μL) in tetrahydrofuran (50 mL) was heated to 50° C. under nitrogen for 1 hour. The solvent was removed in vacuo. The residue was triturated with isohexane to give 3-{[6-(2,4-difluorophenyl)-2-naphthyl]thio}propanenitrile (5.58 g). 1H NMR (500 MHz, CDCl3) δ 7.94 (1H, s), 7.90 (1H, s), 7.85 (2H, d, J=8.5 Hz), 7.66 (1H, d, J=8.3 Hz), 7.50 (2H, d, J=8.6 Hz), 7.00 (1H, dd, J=2.3, 8.6 Hz), 6.96 (1H, d, J=1.9 Hz), 3.24 (2H, t, J=7.2 Hz), 2.64 (2H, t, J=7.3 Hz).

Provenance & Evidence