Reaktion #11105

Reaktionsgleichung

2-bromo-9,9-dimethyl-9H-fluorene

4-chloroaniline

sodium tert-butoxide

rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl

→

amine

(4′-chlorophenyl)-(9,9-dimethyl-9H-fluoren-2-yl)-amine

Lösungsmittel

hexane

1,4-dioxane

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeA 500 ml, 5-neck reaction flask
2. 2
   TemperaturThis mixture was heated
3. 3
   Temperaturto cool to room temperature
4. 4
   workup.ADDITIONpoured into a beaker
5. 5
   SonstigeResidual solids were removed by filtration
6. 6
   Waschenthe filter cake washed with hexane (300 ml)
7. 7
   EinengenThe combined organic filtrate and washings were concentrated
8. 8
   Sonstigeto yield a black/brown oil which
9. 9
   Sonstigewas purified
10. 10
    Sonstigeby dry flash column chromatography

Vorschrift

A 500 ml, 5-neck reaction flask was charged with 2-bromo-9,9-dimethyl-9H-fluorene (25.0 g) (as prepared above), 4-chloroaniline (12.9 g), sodium tert-butoxide (12.3 g), rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (rac-BINAP) (0.4 g), tris(dibenzylideneacetone)-dipalladium(0) (Pd2(dba)3) (0.2 g) and 1,4-dioxane (180 ml). This mixture was heated with stirring to 80° C. and held at this temperature for 66 hours, after which time the reaction was deemed complete as indicated by TLC analysis. The reaction mixture was allowed to cool to room temperature and then poured into a beaker containing hexane (1 litre). Residual solids were removed by filtration and the filter cake washed with hexane (300 ml). The combined organic filtrate and washings were concentrated to yield a black/brown oil which was purified by dry flash column chromatography. The title amine was isolated as a red/brown viscous oil. (12.8 g). iii) Preparation of N,N-bis(4-chlorophenyl)-(9,9-dimethyl-9H-fluoren-2-yl)-amine

Quelle