Thionyl Chloride → 4-(Chloromethyl)-1-(fluoromethoxy)-2-(trifluoromethyl)benzene

HRID 515711Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 515711
[F:1][CH2:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10]O)=[CH:6][C:5]=1[C:12]([F:15])([F:14])[F:13].S(Cl)([Cl:18])=O>>[Cl:18][CH2:10][C:7]1[CH:8]=[CH:9][C:4]([O:3][CH2:2][F:1])=[C:5]([C:12]([F:15])([F:14])[F:13])[CH:6]=1

Komponenten

3

Edukt 2

HCID 24386Thionyl ChlorideHCID 67250584(4-(Fluoromethoxy)-3-(trifluoromethyl)phenyl)methanol

Produkt 1

HCID 668477234-(Chloromethyl)-1-(fluoromethoxy)-2-(trifluoromethyl)benzeneAusbeute 80,3 %

Versuchsvorschrift

(4-(Fluoromethoxy)-3-(trifluoromethyl)phenyl)methanol (1.84 g, 8.21 mmol) was dissolved in thionyl chloride (8.09 mL, 111 mmol) and stirred for 3 h. The reaction was taken up in hexanes and washed with water (twice), saturated NaHCO3, and water. The organics were dried over MgSO4, filtered and concentrated under vacuum to give the title compound as a solid (1.60 g). 1H NMR (400 MHz, DMSO-d6) δ ppm 4.83 (s, 2H), 5.83-6.14 (d, J=53.1 Hz, 2H), 7.46 (d, J=8.46 Hz, 1H), 7.69-7.87 (m, 2H).

Aufarbeitung

  1. washwashed with water (twice), saturated NaHCO3, and water
  2. dry with materialThe organics were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-b76405ddbc2a4510b29d4cdca064efb8
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09108969B2

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