(2E)-3-(4-{[4-Chloro-3-(trifluoromethyl)phenyl]oxy}phenyl)-2-propenenitrile → 3-(4-(4-Chloro-3-(trifluoromethyl)phenoxy)phenyl)propanenitrile

HRID 705807Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12](/[CH:15]=[CH:16]/[C:17]#[N:18])=[CH:11][CH:10]=2)=[CH:4][C:3]=1[C:19]([F:22])([F:21])[F:20]>C1COCC1.[Pd]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17]#[N:18])=[CH:11][CH:10]=2)=[CH:4][C:3]=1[C:19]([F:20])([F:21])[F:22]

Participants

Conditions

Temperature: 25 °C

Procedure

The mixture of (2E)-3-(4-{[4-chloro-3-(trifluoromethyl)phenyl]oxy}phenyl)-2-propenenitrile (18.0 g, 55.6 mmol) and Pd/C (2.00 g, 1.88 mmol) in THF (150 mL) was stirred at 25° C. under H2 overnight, filtered through a pad of Celite, and concentrated. Purification via a column chromatography afforded the title compound as a white solid (15 g).

Workup

filtrationfiltered through a pad of Celite
concentrationconcentrated
customPurification via a column chromatography

Sources & evidence

ORD record: ord-9709c0dfddc1463993aa6dc180132a42
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09174968B2

Reaction notes

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