Water → 4-Chloro-2-fluoro-5-methoxybenzyl chloride

HRID 1385965Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1385965
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[O:9][CH3:10].CO[CH2:13][Cl:14].O>ClCCl.[Ti](Cl)(Cl)(Cl)Cl>[Cl:1][C:2]1[C:3]([O:9][CH3:10])=[CH:4][C:5]([CH2:13][Cl:14])=[C:6]([F:8])[CH:7]=1

Komponenten

6

Edukt 3

HCID 962WaterHCID 7864Chloromethyl Methyl EtherHCID 27735802-Chloro-4-fluoroanisole

Produkt 1

HCID 184083444-Chloro-2-fluoro-5-methoxybenzyl chlorideAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 24193Titanium TetrachlorideLösungsmittel

Versuchsvorschrift

17.6 g (0.11 mol) of 2-chloro-4-fluoroanisole was dissolved in a dichloromethane solution of 1N titanium tetrachloride, and 88.3 g (1.10 mol) of methoxymethyl chloride was dropwise added thereto at room temperature, followed by stirring at room temperature for 5 hours. After completion of the reaction, the reaction solution was poured into water, followed by stirring at room temperature for 2 hours, and then the aqueous phase was removed. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off. Then, the obtained residue was purified by silica gel column chromatography to obtain 15.5 g (yield: 68%) of the desired product. 1H-NMR (300 MHz, CDCl3) δ value: 3.89(3H,s), 5.00(2H,s), 6.97(1H,d), 7.18(1H,d)ppm.

Aufarbeitung

  1. additionwas dropwise added
  2. customat room temperature
  3. customAfter completion of the reaction
  4. stirringby stirring at room temperature for 2 hours
  5. customthe aqueous phase was removed
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off
  8. customThen, the obtained residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-8d3cc4102c894768b026be5c372c6ed1
Quelldatensatz
uspto-grants-2001_07
Patentnummer
US06265349B1

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