Thionyl Chloride → 4-(Chloromethyl)-2-(1,1-dimethylethyl)-3'-(methyloxy)-1,1'-biphenyl

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Reaktionsgleichung

[CH3:1][C:2]([C:5]1[CH:10]=[C:9]([CH2:11]O)[CH:8]=[CH:7][C:6]=1[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=1)([CH3:4])[CH3:3].S(Cl)([Cl:23])=O>C(Cl)Cl>[Cl:23][CH2:11][C:9]1[CH:8]=[CH:7][C:6]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=2)=[C:5]([C:2]([CH3:4])([CH3:3])[CH3:1])[CH:10]=1

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

A dry, round bottom flask containing 12.2 (0.82 g, 3.04 mmol) and DCM (8.5 mL) was cooled to 0° C. After 15 minutes, thionyl chloride (1.50 mL, 20.56 mmol) was carefully added dropwise at 0° C. Upon complete addition of thionyl chloride, the mixture was allowed to warm to room temperature and stirred overnight. After 25 hours, the reaction was concentrated under reduced pressure. The residue was then purified by flash chromatography (SiO2 gel 60, eluted with 0%-15% EtOAc in hexanes). Fractions containing the desired product were combined and concentrated to provide 12.3 as a colorless oil (0.82, 93%). 1H NMR (500 MHz, CDCl3) δ ppm 7.53 (1H, d, J=1.7 Hz), 7.28 (3H, m), 7.03 (1H, d, J=7.8 Hz), 6.90 (3H, m), 4.65 (2H, s), 3.82 (3H, s), 1.23 (9H, s).

Aufarbeitung

temperatureto warm to room temperature
waitAfter 25 hours
concentrationthe reaction was concentrated under reduced pressure
customThe residue was then purified by flash chromatography (SiO2 gel 60, eluted with 0%-15% EtOAc in hexanes)
additionFractions containing the desired product
concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag: ord-11d38465f9414924ac655379dc63a1d2
Quelldatensatz: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08030354B2

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