Bromide ion → 2-Cyanobenzyltriphenylphosphonium bromide

HRID 11076

Reaktionsgleichung

Reaktionsgleichung von HRID 11076
[C:1]1([CH3:9])[C:2]([C:7]#[N:8])=[CH:3][CH:4]=[CH:5][CH:6]=1.C1C(=O)N([Br:17])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C.[Br-].[C:31]1([P:37]([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>C(Cl)Cl.C1C=CC=CC=1>[Br-:17].[C:7]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=1[CH2:9][P+:37]([C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1)([C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)#[N:8]

Komponenten

6

Edukt 4

HCID 259Bromide ionHCID 107212-MethylbenzonitrileHCID 11776TriphenylphosphineHCID 86630000Nbs aibn

Produkt 1

HCID 105999462-Cyanobenzyltriphenylphosphonium bromideAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 1

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

Versuchsvorschrift

Bromination of o-tolunitrile with NBS/AIBN, followed by reaction of the crude bromide with triphenylphosphine (1.2 equiv.), using the procedure described in example 102, except that the reaction time for the bromination was 2 h, gave the phosphonium salt (547) (70%) as a light brown powder, mp (CH2Cl2/benzene) 237–241° C. 1H NMR (CDCl3) δ 7.90 (dd, J=7.8, 2.3 Hz, 1H), 7.85–7.63 (m, 15H), 7.52 (br t, J=7.7 Hz, 1H), 7.44 (br d, J=7.5 Hz, 1H), 7.38 (tdd, J=7.6, 2.1, 1.0 Hz, 1H), 5.86 (d, J=14.7 Hz, 2H). Found: C, 67.88; H, 4.42; N, 3.09. C26H21BrNP requires C, 68.13; H, 4.62; N, 3.06.

Quellen und Nachweise

ORD-Eintrag
ord-a45e48d54ee2440894b7512541d2c34c
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07094798B1

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