Reaction #70673

Reaction equation

2-(3-bromophenyl)-1,3-dioxolane

1-naphthylamine

Sodium tert-butoxide

tri-tert-butylphosphine

→

N-(3-(1,3-dioxolan-2-yl)phenyl)naphthalen-1-amine

Solvents

toluene

Conditions

Workup

1. 1
   OtherA clean and dry 500 ml round bottom flask
2. 2
   Otherequipped with a reflux condenser, magnetic stir bar
3. 3
   Otherthermometer with adapter was prepared
4. 4
   Otherpurged with nitrogen Anhydrous toluene (250.0 ml)
5. 5
   Otherwas transferred to this flask by cannula
6. 6
   OtherThe reaction solution was purged with a strong nitrogen flow for 30 minutes
7. 7
   TemperatureThe vessel was heated
8. 8
   Temperatureto reflux for approximately 5 hours
9. 9
   Filtrationfiltered through a Celite and silica gel pad
10. 10
    Washwashing thoroughly with acetone and chloroform
11. 11
    OtherSolvent was removed by rotary evaporation
12. 12
    OtherThe crude material was purified by flash column chromatography

Procedure

A clean and dry 500 ml round bottom flask equipped with a reflux condenser, magnetic stir bar, and thermometer with adapter was prepared and purged with nitrogen Anhydrous toluene (250.0 ml) was transferred to this flask by cannula. 2-(3-bromophenyl)-1,3-dioxolane (6.0 ml, 0.0397 mol) was added by syringe followed by the manual addition of 1-naphthylamine (5.08 g, 0.0355 mol). The reaction solution was purged with a strong nitrogen flow for 30 minutes. Sodium tert-butoxide (5.60 g, 0.0583 mol) and Pd2dba3 (0.65 g, 0.0007 mol) were then added manually, followed by the addition of tri-tert-butylphosphine (1.30 g, 0.0064 mol) in toluene (˜10 ml) via syringe. The vessel was heated to reflux for approximately 5 hours. The reaction was then cooled to room temperature and filtered through a Celite and silica gel pad washing thoroughly with acetone and chloroform. Solvent was removed by rotary evaporation. The crude material was purified by flash column chromatography using ethyl acetate/hexane as an eluent. This provided pure product confirmed by NMR spectroscopy.

Source