Reaktion #603669

Reaktionsgleichung

N-phenylnaphthalen-1-amine

1-bromo-4-iodobenzene

tri-tert-butylphosphine

sodium tert-butoxide

→

Compound 4

Ausbeute 62.0%

N-(4-bromophenyl)-N-phenylnaphthalen-1-amine

Ausbeute 62.0%

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeCompound 4 [Xu, H.; Yin, K.; Huang, W. Chem. Eur. J. 2007, 13(36), 10281-10293] was prepared
2. 2
   Sonstigewas degassed with argon for about 40 min
3. 3
   workup.STIRRINGwhile stirring
4. 4
   Sonstigeconsumption of the starting material by TLC (SiO2, 100% hexanes)
5. 5
   Temperaturthe reaction was cooled to RT
6. 6
   workup.ADDITIONpoured over EtOAc (ca. 300 mL)
7. 7
   WaschenThe organics were then washed with sat. NaHCO3, H2O (2×) and brine
8. 8
   Trocknendried over MgSO4
9. 9
   Filtrationfiltered
10. 10
    Einengenconcentrated in vacuo
11. 11
    SonstigePurification of the crude product via flash chromatography (SiO2, 8:1-hexanes:CH2Cl2)

Vorschrift

Compound 4 [Xu, H.; Yin, K.; Huang, W. Chem. Eur. J. 2007, 13(36), 10281-10293] was prepared as follows: a mixture of N-phenylnaphthalen-1-amine (2.767 g, 12.62 mmol), 1-bromo-4-iodobenzene (7.140 g, 25.24 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.578 g, 0.631 mmol), tri-tert-butylphosphine (10 wt. % in hexanes) (5.83 mL, 1.89 mmol), sodium tert-butoxide (NaOtBu) (3.032 g, 31.55 mmol) and anhydrous toluene (80 mL) was degassed with argon for about 40 min while stirring. The reaction mixture was then maintained under argon at about 85° C. while stirring. Upon confirming consumption of the starting material by TLC (SiO2, 100% hexanes), the reaction was cooled to RT and poured over EtOAc (ca. 300 mL). The organics were then washed with sat. NaHCO3, H2O (2×) and brine, dried over MgSO4, filtered and concentrated in vacuo. Purification of the crude product via flash chromatography (SiO2, 8:1-hexanes:CH2Cl2) provided Compound 4 (2.93 g, 62%) as a white foam: confirmed by LCMS (APCI): calculated for C22H16BrN (M+): 374; Found: 374.

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