Iodine → 4-Iodo-2-n-propylaniline

Temperature

10 °C

To a solution of 2-n-propylaniline in MeOH (25 mL) was added a solution of NaHCO3 (5.0 g, 59.5 mmol) in H2O (25 mL). Iodine (8.4 g, 33.3 mmol) was added portionwise over 70 min. while maintaining the temp. at 10° C., then the mixture was allowed to stir at 10° C. for 30 min. The resulting mixture was diluted with H2O (30 mL) and extracted with EtOAc (4×40 mL). The combined organic layers were sequentially washed with a 5% Na2S2O3 solution (30 mL) and a saturated NaHCO3 solution (30 mL), dried (Na2SO4), and concentrated under reduced pressure to give 4-iodo-2-n-propylaniline (9.4 g, 98%): TLC (20% EtOAc/hex) Rf0.43. This material was used in the next step without further purification.

1. temperaturewhile maintaining the temp
2. customat 10° C.
3. extractionextracted with EtOAc (4×40 mL)
4. washThe combined organic layers were sequentially washed with a 5% Na2S2O3 solution (30 mL)
5. dry with materiala saturated NaHCO3 solution (30 mL), dried (Na2SO4)
6. concentrationconcentrated under reduced pressure

ORD record

ord-69ae2d4f7ec34da68b4a3f828bf7c267

Source dataset

uspto-grants-2002_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06353006B1