Thionyl Chloride → 1-(Chloromethyl)-2-fluoro-5-methoxy-4-nitrobenzene

HRID 1947893Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1947893
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([O:11][CH3:12])=[CH:4][C:3]=1[CH2:13]O.S(Cl)([Cl:17])=O>C(Cl)Cl>[Cl:17][CH2:13][C:3]1[CH:4]=[C:5]([O:11][CH3:12])[C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=1[F:1]

Komponenten

4

Edukt 2

HCID 24386Thionyl ChlorideHCID 67255286(2-Fluoro-5-methoxy-4-nitrophenyl)methanol2×

Produkt 1

HCID 672551071-(Chloromethyl)-2-fluoro-5-methoxy-4-nitrobenzene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of (2-fluoro-5-methoxy-4-nitrophenyl)methanol (Compound 130D, 1.45 g, 7.21 mmol) in anhydrous DCM (17.0 mL) was charged with Thionyl chloride (1.055 mL, 14.5 mmol). and stirred while refluxing for 16 h. The reaction mixture was concentrated under reduced pressure to yield a brown solid. This material was used without any further purification. 1H NMR (CDCl3, 400 MHz): δ=3.99 (s, 3H), 4.65 (d, J=1.01 Hz, 2H), 7.19 (d, J=5.81 Hz, 1H), 7.65 (d, J=8.84 Hz, 1H).

Aufarbeitung

  1. temperaturewhile refluxing for 16 h
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customto yield a brown solid
  4. customThis material was used without any further purification

Quellen und Nachweise

ORD-Eintrag
ord-d946f88d850644c4aceac82c8046a2d2
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08399433B2

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