Reaktion #79864

ord-f03eee2555c84e3d88d2ab1967ae23fe

Reaktionsgleichung

CC1(C)OB(c2ccc(Oc3ccccc3)c(C#N)c2)OC1(C)C
2-phenoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)benzonitrile
O=[N+]([O-])c1cc(Br)ccc1Oc1ccccc1
4-bromo-2-nitro-1-phenoxybenzene
COC(=O)[C@H]1[C@H]2C[C@@H]3c4[nH]c5cc(OC)ccc5c4CCN3C[C@H]2C[C@@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)[C@@H]1OC
Hypersil
→
CC1(C)OB(c2ccc(Oc3ccccc3)c([N+](=O)[O-])c2)OC1(C)C
title compound
CC1(C)OB(c2ccc(Oc3ccccc3)c([N+](=O)[O-])c2)OC1(C)C
2-Nitro-4-(4,4,5,5-tetrametyl-1,3,2-dioxaborolan-2-yl)phenyl Phenyl Ether

Edukte

CC1(C)OB(c2ccc(Oc3ccccc3)c(C#N)c2)OC1(C)C
2-phenoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)benzonitrile
O=[N+]([O-])c1cc(Br)ccc1Oc1ccccc1
4-bromo-2-nitro-1-phenoxybenzene
COC(=O)[C@H]1[C@H]2C[C@@H]3c4[nH]c5cc(OC)ccc5c4CCN3C[C@H]2C[C@@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)[C@@H]1OC
Hypersil

Reagenzien

Keine

Lösungsmittel

CC#N
acetonitrile

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigetr 14.02 min.

Vorschrift

The title compound was prepared in a 56% from 4-bromo-2-nitro-1-phenoxybenzene in a similar manner to that described for the preparation 2-phenoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)benzonitrile: 1H NMR (DMSO-d6, 400 MHz) δ 8.19(d, 1H), 7.91(d, 1H), 7.46(t, 2H), 7.27(t, 1H), 7.14(d, 2H), 7.06(d, 1H), 1.31(s, 12H); RP-HPLC (Hypersil HS, 5 μm, 100 A 4.6×250 mm; 25%-100% acetonitrile—0.05 M ammonium acetate over 10 min, 1 ml/min) tr 14.02 min.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06713474B2uspto-grants-2004_03