Reaktion #79867

ord-e0cc202f360b44c5bc1257f5b922c4bb

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=Cc1ccc(Br)cc1Oc1ccccc1
4-bromo-2-phenoxybenzaldehyde
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(C=O)c2)OC1(C)C
title compound
CC1(C)OB(c2ccc(Oc3ccccc3)c(C=O)c2)OC1(C)C
2-Phenoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde

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=Cc1ccc(Br)cc1Oc1ccccc1
4-bromo-2-phenoxybenzaldehyde
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.

Vorschrift

The title compound was prepared in a 62% from 4-bromo-2-phenoxybenzaldehyde 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 10.43(s, 1H), 8.14(s, 1H), 7.89(d, 1H), 7.48(t, 2H), 7.27(t, 1H), 7.20(d, 2H), 6.88(d, 1H), 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 14.02min.

Quelle

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