Reaktion #11244

ord-9d994210277644129c424413fa4c52d0

Reaktionsgleichung

COc1cc([N+](=O)[O-])ccc1CO
(2-methoxy-4-nitrophenyl)methanol
Br
HBr
[Br-]
bromide
c1ccc(P(c2ccccc2)c2ccccc2)cc1
triphenylphosphine
COc1cc([N+](=O)[O-])ccc1C[P+](c1ccccc1)(c1ccccc1)c1ccccc1.[Br-]
phosphonium
Ausbeute 84.0%
COc1cc([N+](=O)[O-])ccc1C[P+](c1ccccc1)(c1ccccc1)c1ccccc1.[Br-]
(2-Methoxy-4-nitrobenzyl)(triphenyl)phosphonium bromide
Ausbeute 84.0%

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    workup.WAITfollowed by 1 day at 55° C.

Vorschrift

Bromination of (2-methoxy-4-nitrophenyl)methanol with 30% HBr in acetic acid, followed by reaction of the crude bromide with triphenylphosphine, using the procedure described in example 112, except that the conditions for the displacement were 3 days at 20° C. followed by 1 day at 55° C., gave the phosphonium salt (582) (84%) as a yellow solid, mp (CH2Cl2/benzene) 194–196° C. 1H NMR (CDCl3) δ 7.83–7.63 (m, 17H), 7.45 (br s, 1H), 5.52 (d, J=15.0 Hz, 2H). Found: C, 61.10; H, 4.73; N, 3.05. C26H23BrNO3P requires C, 61.43; H, 4.56; N, 2.76.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07094798B1uspto-grants-2006_08