Reaktion #79854

ord-ff11ae08660144859675c170f1c5e7a9

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
Clc1cc(Br)ccc1Oc1ccccc1
4-bromo-2-chloro-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(Cl)c2)OC1(C)C
title compound
Ausbeute 81.0%
CC1(C)OB(c2ccc(Oc3ccccc3)c(Cl)c2)OC1(C)C
2-(3-Chloro-4-phenoxyphenyl)-4,4,5,5-tetrametyl-1,3,2-dioxaborolane
Ausbeute 81.0%

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
Clc1cc(Br)ccc1Oc1ccccc1
4-bromo-2-chloro-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 15.53 min.

Vorschrift

The title compound (472 mg, 81%) was prepared from 4-bromo-2-chloro-1-phenoxybenzene (500 mg, 1.77 mmol) 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 7.75(s, 1H), 7.60 (d, 1H), 7.42(t, 2H), 7.21(t, 1H), 7.02 (m, 3H), 1.30(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 15.53 min.

Quelle

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