Perfluorocyclopentene → 4-(5-(4-Methoxyphenyl)-4-(perfluorocyclopent-1-en-1-yl)thiophen-2-yl)benzonitrile

HRID 589240

Reaktionsgleichung

Br[C:2]1[CH:3]=[C:4]([C:15]2[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][CH:16]=2)[S:5][C:6]=1[C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1.[Li]CCCC.CCCCCC.[F:34][C:35]1([F:46])[C:39]([F:40])=[C:38](F)[C:37]([F:43])([F:42])[C:36]1([F:45])[F:44]>C1COCC1>[CH3:14][O:13][C:10]1[CH:11]=[CH:12][C:7]([C:6]2[S:5][C:4]([C:15]3[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][CH:16]=3)=[CH:3][C:2]=2[C:38]2[C:37]([F:43])([F:42])[C:36]([F:44])([F:45])[C:35]([F:34])([F:46])[C:39]=2[F:40])=[CH:8][CH:9]=1

Komponenten

Reaktionsbedingungen

Temperatur: -50 °C

Versuchsvorschrift

To a solution of (57) (5.0 g, 13.50 mmol) in dry THF (300 mL) was slowly added n-BuLi hexane solution (2.0 M, 7.43 mL, 14.85 mmol) at −50° C. under an argon atmosphere. The solution was stirred for 15 minutes at −50° C. After the addition of octafluorocyclopentene (5.44 mL, 40.5 mmol), the reaction mixture was stirred for 2 h. The reaction was quenched by the addition of methanol and warmed to RT. The solvents were removed by rotary evaporation and flash chromatography (10% EtOAc in hexanes) afforded a dark yellow oil (4.0 g, 61.3%).

Aufarbeitung

customat −50° C.
stirringthe reaction mixture was stirred for 2 h
customThe reaction was quenched by the addition of methanol
temperaturewarmed to RT
customThe solvents were removed by rotary evaporation and flash chromatography (10% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag: ord-744b12cc877b4a8f908799df7ca9ca1a
Quelldatensatz: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09227986B2

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