Potassium Carbonate → 5-Bromo-[1,1'-biphenyl]-3-carbonitrile

Reaktionsgleichung

Br[C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Br:10])[CH:9]=1)[C:5]#[N:6].[C:11]1(B(O)O)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C([O-])([O-])=O.[K+].[K+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.COCCOC>[Br:10][C:8]1[CH:7]=[C:4]([C:5]#[N:6])[CH:3]=[C:2]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:9]=1

Komponenten

Reaktionsbedingungen

Temperatur: 95 °C

Versuchsvorschrift

A mixture of 3,5-dibromobenzonitrile (0.58 g, 2.2 mmol), phenylboronic acid (0.24 g, 2.0 mmol), Pd(PPh3)4 (0.23 g, 0.1 mmol), K2CO3 (3 mL 2 M aqueous solution) and DME (3 mL) was degassed and heated to 95° C. for 12 hr under argon. The reaction mixture was diluted with EtOAc and washed with water. The aqueous layer was extracted with ethyl acetate (2×). The combined organics were dried (MgSO4) and concentrated to give the crude product which was purified with chromatography on silica gel (EtOAc/hexanes) to afford 5-bromobiphenyl-3-carbonitrile.

Aufarbeitung

customwas degassed
additionThe reaction mixture was diluted with EtOAc
washwashed with water
extractionThe aqueous layer was extracted with ethyl acetate (2×)
dry with materialThe combined organics were dried (MgSO4)
concentrationconcentrated
customto give the crude product which
customwas purified with chromatography on silica gel (EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag: ord-1e2a8c379d8f4263801b1fe97805a5f2
Quelldatensatz: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08530480B2

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