Ethanol → 4-Chloro-3-iodoaniline

Temperature

22 °C

1-Chloro-2-iodo-4-nitro-benzene (2.00 g, 7.09 mmol) was dissolved in THF (30 mL) at 60° C. and EtOH (35 mL) was added followed by NH4Cl (0.569 g, 10.6 mmol in 30 mL of water) and iron powder (1.58 g, 28.4 mmol). This mixture was stirred vigorously for 3 h and then cooled in 22° C. and filtered though celite rinsing with EtOAc. The solution was then concentrated to ˜30 mL in vacuo and then poured into a 1:1 solution of 1N NaOH/brine (100 mL). This mixture was then extracted with EtOAc (3×50 mL) and the organics were dried over anhydrous MgSO4. Filtration and concentration gave compound 801B as a yellow solid. No purification was necessary. HPLC: 100% at 2.310 min (retention time) (YMC S5 ODS column 4.6×50 mm eluting with 10-90% aqueous methanol over 4 mincontaining 0.2% phosphoric acid, 4 mL/min, monitoring at 220 nm), MS (ES): m/z 517.6 [M+Na]+.

1. filtrationfiltered
2. washthough celite rinsing with EtOAc
3. concentrationThe solution was then concentrated to ˜30 mL in vacuo
4. additionpoured into a 1:1 solution of 1N NaOH/brine (100 mL)
5. extractionThis mixture was then extracted with EtOAc (3×50 mL)
6. dry with materialthe organics were dried over anhydrous MgSO4
7. filtrationFiltration and concentration

ORD record

ord-7fde067f351b4bb8b440cd8d8ec6942c

Source dataset

uspto-grants-2009_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07517904B2