Réaction #11105

Équation de réaction

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

Solvants

hexane

1,4-dioxane

Conditions de réaction

Traitement

1. 1
   AutreA 500 ml, 5-neck reaction flask
2. 2
   TempératureThis mixture was heated
3. 3
   Températureto cool to room temperature
4. 4
   workup.ADDITIONpoured into a beaker
5. 5
   AutreResidual solids were removed by filtration
6. 6
   Lavagethe filter cake washed with hexane (300 ml)
7. 7
   ConcentrationThe combined organic filtrate and washings were concentrated
8. 8
   Autreto yield a black/brown oil which
9. 9
   Autrewas purified
10. 10
    Autreby dry flash column chromatography

Mode opératoire

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

Source