Reaktion #11168

ord-45cd2ce8b12c4a538ef3a33a64d2aec4

Reaktionsgleichung

COc1ccc(Cl)c(CO)c1Cl
(2,6-dichloro-3-methoxyphenyl)methanol
Br
HBr
[Br-]
bromide
c1ccc(P(c2ccccc2)c2ccccc2)cc1
triphenylphosphine
COc1ccc(Cl)c(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)c1Cl.[Br-]
phosphonium
Ausbeute 97.0%
COc1ccc(Cl)c(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)c1Cl.[Br-]
(2,6-Dichloro-3-methoxybenzyl)(triphenyl)phosphonium bromide
Ausbeute 97.0%

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

Bromination of (2,6-dichloro-3-methoxyphenyl)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 reaction time for the displacement was 36 h, gave the phosphonium salt (526) (97%) as a white solid, mp (CH2Cl2/benzene) 242–244° C. 1H NMR (CDCl3) δ 7.83–7.60 (m, 15H), 7.15 (dd, J=9.1, 0.8 Hz, 1H), 6.88 (dd, J=9.0, 2.4 Hz, 1H), 5.41 (d, J=14.3 Hz, 2H), 3.84 (s, 3H). Found: C, 58.68; H, 4.16. C26H22BrCl2OP requires C, 58.67; H, 4.17.

Quelle

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