4-Fluorostyrene → 3-({4-[(E)-2-(4-fluorophenyl)vinyl]phenyl}sulfonyl)propanenitrile

HRID 1351619Notes

Reaction equation

C([O-])(=O)C.[Na+].[F:6][C:7]1[CH:14]=[CH:13][C:10]([CH:11]=[CH2:12])=[CH:9][CH:8]=1.Br[C:16]1[CH:21]=[CH:20][C:19]([S:22]([CH2:25][CH2:26][C:27]#[N:28])(=[O:24])=[O:23])=[CH:18][CH:17]=1>CN1CCCC1=O.O.CCOC(C)=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:6][C:7]1[CH:14]=[CH:13][C:10](/[CH:11]=[CH:12]/[C:16]2[CH:21]=[CH:20][C:19]([S:22]([CH2:25][CH2:26][C:27]#[N:28])(=[O:23])=[O:24])=[CH:18][CH:17]=2)=[CH:9][CH:8]=1

Participants

Conditions

Temperature: 135 °C

Procedure

To a suspension of sodium acetate (54 g, 0.66 mol) and 4-fluorostyrene (90 g, 0.74 mol) in 1-methyl-2-pyrrolidinone (500 mL) was added 3-[(4-bromophenyl)sulfonyl]propanenitrile (Step 1, 90 g, 0.33 mol) and palladium (II) acetate (1.4 g, 6.2 mmol). The mixture was plunged into an oil-bath at 100° C. and heated to 135° C. for 20 minutes. The cooled reaction mixture was diluted with water and EtOAc and filtered through Hyflo®. The organic layer of the filtrate was washed with water (×3) then concentrated in vacuo. The residue was triturated with isohexane to give 3-({4-[(E)-2-(4-fluorophenyl)vinyl]phenyl}sulfonyl)propanenitrile (73 g). δH (360 MHz, CDCl3): 7.88 (2H, d, J 8.0), 7.69 (2H, d, J 8.3), 7.51 (2H, dd, J 5.6, 8.3), 7.22 (1H, d, J 15.0), 7.10–7.02 (3H, m), 3.39 (2H, t, J 7.7), 2.83 (2H, t, J 7.7).

Workup

customThe mixture was plunged into an oil-bath at 100° C.
customThe cooled reaction mixture
filtrationfiltered through Hyflo®
washThe organic layer of the filtrate was washed with water (×3)
concentrationthen concentrated in vacuo
customThe residue was triturated with isohexane

Sources & evidence

ORD record: ord-f301a6d1391d40b5a6fcb3dda51a62dd
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07217740B2

Reaction notes

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