반응 #11105

반응 방정식

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

용매

hexane

1,4-dioxane

반응 조건

후처리

1. 1
   기타A 500 ml, 5-neck reaction flask
2. 2
   온도This mixture was heated
3. 3
   온도to cool to room temperature
4. 4
   workup.ADDITIONpoured into a beaker
5. 5
   기타Residual solids were removed by filtration
6. 6
   세척the filter cake washed with hexane (300 ml)
7. 7
   농축The combined organic filtrate and washings were concentrated
8. 8
   기타to yield a black/brown oil which
9. 9
   기타was purified
10. 10
    기타by dry flash column chromatography

실험 절차

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

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