反応 #11105

反応方程式

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

溶媒

hexane

1,4-dioxane

反応条件

後処理

1. 1
   その他A 500 ml, 5-neck reaction flask
2. 2
   温度This mixture was heated
3. 3
   温度to cool to room temperature
4. 4
   workup.ADDITIONpoured into a beaker
5. 5
   その他Residual solids were removed by filtration
6. 6
   洗浄the filter cake washed with hexane (300 ml)
7. 7
   濃縮The combined organic filtrate and washings were concentrated
8. 8
   その他to yield a black/brown oil which
9. 9
   その他was purified
10. 10
    その他by dry flash column chromatography

実験手順

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

出典