Reaction #60235

Reaction equation

sodium t-butoxide

2-bromo-7-iodo-9,9-dimethylfluorene

diphenylamine

N,N′-dimethylethylene-diamine

→

yellow solid

Yield 69.9%

2-(N,N-diphenylamino)-7-bromo-9,9-dimethylfluorene

Yield 69.9%

Solvents

xylene

Conditions

Workup

1. 1
   workup.ADDITIONCharged under Ar atmosphere
2. 2
   Temperaturethe mixture was refluxed for 24 hours
3. 3
   Temperatureunder heating
4. 4
   Extractionthe mixture was extracted with toluene
5. 5
   Filtrationthe insoluble matter was filtered
6. 6
   ConcentrationThe filtrate was concentrated

Procedure

Charged under Ar atmosphere were 2-bromo-7-iodo-9,9-dimethylfluorene 20.0 g, diphenylamine 8.46 g, copper iodide 0.476 g, N,N′-dimethylethylene-diamine 0.441 g, sodium t-butoxide 7.21 g and xylene 50 ml, and the mixture was refluxed for 24 hours under heating. After cooled down to room temperature, the mixture was extracted with toluene, and the insoluble matter was filtered. The filtrate was concentrated, and then the concentrate was refined by silica gel chromatography to obtain 15.4 g of a yellow solid matter of 2-(N,N-diphenylamino)-7-bromo-9,9-dimethylfluorene.

Source