Benzoyl Peroxide → 4,6-Dibromo-3-(bromomethyl)-2-(2,4-difluorophenyl)pyridine

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Reaktionsgleichung

[Br:1][C:2]1[CH:7]=[C:6]([Br:8])[N:5]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=2[F:16])[C:3]=1[CH3:17].[Br:18]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:7]=[C:6]([Br:8])[N:5]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=2[F:16])[C:3]=1[CH2:17][Br:18]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

To a stirred solution of 4,6-dibromo-2-(2,4-difluorophenyl)-3-methylpyridine (5.0 g, 13.77 mmol, 1 eq) in CCl4 (125 mL) was added N-bromosuccinimide (2.95 g, 16.6 mmol 1.2 eq) and benzoyl peroxide (340 mg, 1.37 mmol, 0.1 eq). The mixture was brought to and maintained at reflux until all the starting material was consumed (approx 3.5 h). The reaction mixture was cooled to 0° C. and the succinimide was filtered off. The solvent was removed under reduced pressure and the product was purified by flash column chromatography on silica gel elufing with 2% Et2O in hexanes giving 4,6-dibromo-3-(bromomethyl)-2-(2,4-difluorophenyl)pyridine. Mass spectrum (ESI) 440.1 (M+1); 442.1 (M+3); 444.1 (M+5); 446.1 (M+7). 1H NMR (500 MHz, CDCl3) δCHCl3: 7.84 (1H, s); 7.50 (1H, m); 7.05 (1H, m); 6.96 (1H, m); 4.44 (2H br s).

Aufarbeitung

temperaturemaintained
temperatureat reflux until all the starting material
customwas consumed (approx 3.5 h)
filtrationthe succinimide was filtered off
customThe solvent was removed under reduced pressure
customthe product was purified by flash column chromatography on silica gel elufing with 2% Et2O in hexanes

Quellen und Nachweise

ORD-Eintrag: ord-8c9e8154d86c4d20b1a5188c8134d260
Quelldatensatz: uspto-grants-2004_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06809199B2

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