2-Bromo-5-fluorotoluene → Tert-butyl 4-(4-fluoro-2-methylphenyl)piperazine-1-carboxylate

HRID 84

Reaktionsgleichung

Reaktionsgleichung von HRID 84
CC(C)(C)OC(=O)N1CCNCC1.Cc1cc(F)ccc1Br>Cc1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C([O-])[O-].[Cs+].[Cs+].[Pd].[Pd].c1ccc(P(c2ccccc2)c2ccc3ccccc3c2-c2c(P(c3ccccc3)c3ccccc3)ccc3ccccc23)cc1>Cc1cc(F)ccc1N1CCN(C(=O)OC(C)(C)C)CC1

Komponenten

7

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

In a 200ml flask was added 1-bromo-4-fluoro-2-methylbenzene (2 g, 10.58 mmol) and TERT-BUTYL 1-PIPERAZINECARBOXYLATE (2.365 g, 12.70 mmol), CESIUM CARBONATE (5.17 g, 15.87 mmol) , BINAP (0.791 g, 1.27 mmol) 18-CROWN-6 (0.336 g, 1.27 mmol), followed by toluene (25 ml). Degass the mixture. TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (0.581 g, 0.63 mmol) was added. Heat at 110oC under nitrogen in an oil bath for overnight. The reaction mixture was diluted with ethyl acetate and filtered through celite. The Celite was washed with EtOAC. The EtOAC was concentrated down to give a brown oil. The crude product was purified by silica gel column(40g) and was eluted with 0% EtOAC/Hexane -50% EtOAC/Hexane. Yield: 0.5g Yellow oil.

Quellen und Nachweise

ORD-Eintrag
ord-7ef9bb9d04ab4703a01fe4c2dfba9490
Quelldatensatz
750 AstraZeneca ELN dataset
Originallink
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