Bromide ion → (2-Chloro-3-nitrobenzyl)(triphenyl)phosphonium bromide

HRID 11079

Reaktionsgleichung

Reaktionsgleichung von HRID 11079
[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[CH3:11].C1C(=O)N([Br:19])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C.[Br-].[C:33]1([P:39]([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>C(Cl)Cl.C1C=CC=CC=1>[Br-:19].[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:11][P+:39]([C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1)([C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)[C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Komponenten

6

Edukt 4

HCID 259Bromide ionHCID 11776TriphenylphosphineHCID 775912-Chloro-3-nitrotolueneHCID 86630000Nbs aibn

Produkt 1

HCID 87899071(2-Chloro-3-nitrobenzyl)(triphenyl)phosphonium bromideAusbeute 44 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 23443464Methane, dichloro-, compd. with benzene (1:1)Lösungsmittel

Versuchsvorschrift

Bromination of 2-chloro-3-nitrotoluene with NBS/AIBN, followed by reaction of the crude bromide with triphenylphosphine, using the procedure described in example 102, except that the reaction time for the bromination was 2 h and the displacement reaction was performed at 70° C. for 1 d, gave the phosphonium salt (554) (44%) as a light brown solid, mp (CH2Cl2/benzene) 224–228° C. 1H NMR (CDCl3) δ 8.09 (br d, J=8.3 Hz, 1H), 7.86–7.63 (m, 16H), 7.34 (t, J=8.1 Hz, 1H), 5.95 (d, J=14.6 Hz, 2H). Found: C, 58.68; H, 4.12; N, 2.79. C25H20BrclNO2P requires C, 58.56; H, 3.93; N, 2.73.

Aufarbeitung

  1. customthe displacement reaction
  2. waitwas performed at 70° C. for 1 d

Quellen und Nachweise

ORD-Eintrag
ord-fa1cddeabd1848c58bbff604171a8e90
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07094798B1

Verknüpfte Notizen

Wird geladen…