Reaction #470395

Reaction equation

1-fluoro-2-nitrobenzene

2-aminobiphenyl

potassium fluoride

→

product

Yield 91.1%

N-(2-nitrophenyl)biphenyl-2-amine

Yield 91.1%

Conditions

Workup

1. 1
   Otherwas prepared in a 100 mL round bottom flask
2. 2
   OtherThe flask was evacuated
3. 3
   TemperatureThe reaction mixture was cooled
4. 4
   workup.ADDITIONethyl acetate and water were added
5. 5
   OtherThe layers were separated
6. 6
   Extractionthe aqueous layer was extracted with ethyl acetate
7. 7
   DryingThe organic layers were dried over magnesium sulfate
8. 8
   Filtrationfiltered
9. 9
   Otherevaporated
10. 10
    OtherThe residue was preabsorbed onto Celite
11. 11
    Otherpurified by column chromatography
12. 12
    Washeluting with 0, 2, and 5% ethyl acetate/hexanes

Procedure

A mixture of 1-fluoro-2-nitrobenzene (13.06 g, 92.6 mmol), 2-aminobiphenyl (31.3 g, 185.2 mmol), and potassium fluoride (8.1 g, 138.9 mmol) was prepared in a 100 mL round bottom flask. The flask was evacuated and replaced with nitrogen. The mixture was heated to 200° C. overnight. The reaction mixture was cooled and ethyl acetate and water were added. The layers were separated and the aqueous layer was extracted with ethyl acetate. The organic layers were dried over magnesium sulfate, filtered, and evaporated. The residue was preabsorbed onto Celite and purified by column chromatography eluting with 0, 2, and 5% ethyl acetate/hexanes. 24.5 g (91%) of product was obtained.

Source