Triphenylarsine → 3-Chloro-4-vinyl-phenylamine

Temperature

50 °C

To a deoxygenated solution of 3-chloro-4-iodo-aniline (6.95 g), triphenyl arsine (0.67 g), and tris(dibenzylideneacetone)palladium(O) (0.50 g) in tetrahydrofuran (120 mL) at 50° C. is added tributylvinyltin (10 g) and the mixture is stirred for approximately 15 hours at 50° C. under an atmosphere of argon. The reaction is then cooled, filtered through diatomaceous earth, and the filtrate is evaporated to dryness under reduced pressure. The residue is dissolved in hexanes and then extracted three times with 5% aqueous hydrochloric acid. These aqueous acidic extracts are then basified with solid potassium carbonate and extracted three times with ethyl acetate. These pooled organic extracts are then washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and the solvent is removed under reduced pressure. The resulting residue is chromatographed over silica gel (hexanes and then 10% ethyl acetate in hexanes is used as the eluant) to provide the desired product as an amber oil.

1. temperatureThe reaction is then cooled
2. filtrationfiltered through diatomaceous earth
3. customthe filtrate is evaporated to dryness under reduced pressure
4. dissolutionThe residue is dissolved in hexanes
5. extractionextracted three times with 5% aqueous hydrochloric acid
6. extractionextracted three times with ethyl acetate
7. washThese pooled organic extracts are then washed with saturated aqueous sodium chloride
8. dry with materialdried over anhydrous magnesium sulfate
9. customthe solvent is removed under reduced pressure
10. customThe resulting residue is chromatographed over silica gel (hexanes

ORD record

ord-2800af53a56a49a28e9ecce32f4f3a3a

Source dataset

uspto-grants-2001_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06262090B1