1,2-Bis(chloromethyl)benzene → 2-(Chloromethyl)benzyltriethylphosphonium chloride

HRID 375018

Reaktionsgleichung

Reaktionsgleichung von HRID 375018
[Cl:1][CH2:2][C:3]1[C:4]([CH2:9][Cl:10])=[CH:5][CH:6]=[CH:7][CH:8]=1.[CH2:11]([P:13]([CH2:16][CH3:17])[CH2:14][CH3:15])[CH3:12].[Cl-].C([PH+](CC)CC)C>C1(C)C=CC=CC=1>[Cl-:1].[Cl:10][CH2:9][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[CH2:2][P+:13]([CH2:16][CH3:17])([CH2:14][CH3:15])[CH2:11][CH3:12]

Komponenten

5

Edukt 3

HCID 119191,2-Bis(chloromethyl)benzeneHCID 27365TriethylphosphineHCID 19032181Triethylphosphonium chloride salt

Produkt 1

HCID 190321702-(Chloromethyl)benzyltriethylphosphonium chloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a mixture of α,α'-dichloro-o-xylene (15.0 g, 86.0 mmol) in toluene (200 ml) was added triethylphosphine (6.3 ml, 43.0 mmol) under argon gas. The reaction mixture was stirred for several days at room temperature under argon after which time the triethylphosphonium chloride salt had crystallized out of solution. The crystals were filtered and washed with toluene (3×50 mL) and pentane (3×50 mL) and dried: 1H NMR (CDCl3) δ1.15-1.26 (dt, 9), 2.58-2.69 (m, 6H), 4.39-4.44 (d, 2H), 4.87 (s, 2H) , 7.31-7.34 (dd, 2H) , 7.43-7.46 (dd, 1H), 7.50-7.54 (m, 1H).

Aufarbeitung

  1. customhad crystallized out of solution
  2. filtrationThe crystals were filtered
  3. washwashed with toluene (3×50 mL) and pentane (3×50 mL)
  4. customdried

Quellen und Nachweise

ORD-Eintrag
ord-10ae76f6ec0f4443944228377f5b406d
Quelldatensatz
uspto-grants-1996_01
Patentnummer
US05484556

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