Reaktion #1852029

Reaktionsgleichung

4-Bromo-1-[(3-chloropropyl)sulfanyl]-2-nitrobenzene

→

5-bromo-2-[(3-chloropropyl)sulfanyl]aniline

Ausbeute 73.0%

Lösungsmittel

MeOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction flask was evacuated with nitrogen, and Pd(OH)2 on carbon (400 mg)
2. 2
   workup.ADDITIONwas added
3. 3
   SonstigeThe reaction flask was evacuated with nitrogen several time
4. 4
   FiltrationThe reaction was filtered over a bed of celite
5. 5
   Waschenthe residue was washed with MeOH (5 mL)
6. 6
   EinengenThe supernatant was concentrated
7. 7
   Sonstigethe crude, black residue was purified by column chromatography (50-20% hexanes-CH2Cl2)

Vorschrift

4-Bromo-1-[(3-chloropropyl)sulfanyl]-2-nitrobenzene (1.97 g, 7.1 mmol) was dissolved in MeOH (25 mL). The reaction flask was evacuated with nitrogen, and Pd(OH)2 on carbon (400 mg) was added. The reaction flask was evacuated with nitrogen several time before being subjected to an atmosphere of H2 (50 psi). The flask was shaken on a parr apparatus for 72 hrs. The reaction was filtered over a bed of celite and the residue was washed with MeOH (5 mL). The supernatant was concentrated, and the crude, black residue was purified by column chromatography (50-20% hexanes-CH2Cl2), to afford 5-bromo-2-[(3-chloropropyl)sulfanyl]aniline (1.28 g, 73%) as a clear oil. 1H NMR (CDCl3, 300 Mhz) δ7.20 (d, 1H, 8.0 Hz), 6.88 (d, 1H, 2.0 Hz), 6.79 (dd, 1H, 2.0 Hz, 8.0 Hz), 4.41 (s, 2H), 3.64 (t, 2H, 6.6 Hz), 2.86 (t, 2H, 7.0 Hz), 1.94-1.99 (m, 2H) ppm.

Quelle