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

HRID 735311Notes

Reaction equation

[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH:15]=[C:14]([SH:19])[CH:13]=[CH:12]2.BrC1C=C2C(=CC=1)C=C(O)C=C2.[C:32](#[N:35])[CH:33]=[CH2:34].C(N(CC)CC)C>O1CCCC1>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH:15]=[C:14]([S:19][CH2:34][CH2:33][C:32]#[N:35])[CH:13]=[CH:12]2

Participants

Conditions

Temperature: 50 °C

Procedure

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).

Workup

customThe solvent was removed in vacuo
customThe residue was triturated with isohexane

Sources & evidence

ORD record: ord-d55ed4dcd5bf4cb8b454524ebad300a5
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07592456B2

Reaction notes

Loading…