Tributylphosphine → 4-(Bromomethyl)benzyltri-n-butylphosphonium bromide

HRID 2399648

Reaktionsgleichung

Reaktionsgleichung von HRID 2399648
[CH2:1]([P:5]([CH2:10][CH2:11][CH2:12][CH3:13])[CH2:6][CH2:7][CH2:8][CH3:9])[CH2:2][CH2:3][CH3:4].[Br:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][Br:23])=[CH:18][CH:17]=1>C1(C)C=CC=CC=1>[Br-:14].[Br:23][CH2:22][C:19]1[CH:20]=[CH:21][C:16]([CH2:15][P+:5]([CH2:6][CH2:7][CH2:8][CH3:9])([CH2:10][CH2:11][CH2:12][CH3:13])[CH2:1][CH2:2][CH2:3][CH3:4])=[CH:17][CH:18]=1

Komponenten

4

Edukt 2

HCID 13831TributylphosphineHCID 693351,4-Bis(bromomethyl)benzene

Produkt 1

HCID 676569404-(Bromomethyl)benzyltri-n-butylphosphonium bromide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

A mixture of tri-n-butylphosphine (5.7 g, 28.4 mmol) in toluene (50 mL) was added dropwise to a mixture of α,α'-dibromo-p-xylene (15 g, 56.8 mmol, 2 eq.) in 200 mL of toluene under argon gas. The reaction mixture was allowed to stir for several days at room temperature under argon, after which time the tri-n-butylphosphonium bromide salt had crystallized out of solution. The crystals were filtered and washed three times each with 50 mL portions toluene and hexanes, then air dried: 1H NMR (CDCl3) δ 0.93 (t, 9H), 1.45 (m, 12H), 2.40 (m, 6H), 4.33-4.37 (d, 2H), 4.47 (s, 2H), 7.37-7.40 (d, 2H), 7.46-7.49 (dd, 2H).

Aufarbeitung

  1. customafter which time the tri-n-butylphosphonium bromide salt had crystallized out of solution
  2. filtrationThe crystals were filtered
  3. washwashed three times each with 50 mL portions toluene and hexanes
  4. customair dried

Quellen und Nachweise

ORD-Eintrag
ord-d442b1a4cd88408a9651fc54d77cad49
Quelldatensatz
uspto-grants-1995_09
Patentnummer
US05451347

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