HCID 22735649, compound → 5-Bromo-2-[(3-chloropropyl)sulfanyl]aniline

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.

1. customThe reaction flask was evacuated with nitrogen, and Pd(OH)2 on carbon (400 mg)
2. additionwas added
3. customThe reaction flask was evacuated with nitrogen several time
4. filtrationThe reaction was filtered over a bed of celite
5. washthe residue was washed with MeOH (5 mL)
6. concentrationThe supernatant was concentrated
7. customthe crude, black residue was purified by column chromatography (50-20% hexanes-CH2Cl2)

ORD record

ord-4eddc9ca713d4d24ac918ca5eaf51c2e

Source dataset

uspto-grants-2007_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

USRE039679E1