Sodium Hydroxide → HCID 58053515, compound

Temperature

55 °C

To a solution of 2-chloro-4-methoxypyridine (0.5 g, 3.48 mmol) in sulfuric acid (2.5 mL) was added N-iodosuccinimide (0.825 g, 3.48 mmol) portionwise at room temperature. The mixture was stirred at 55° C. for 2 hours. The reaction mixture was poured into ice water (10 mL) and 8 M NaOH (20 mL) was added slowly, after which the dark brown solution turned pale yellow. The aqueous layer was extracted with CH2Cl2 (2×20 mL). The organic layers were washed with brine (10 mL) and concentrated in vacuo onto silica gel. Dry flash chromatography, eluting with 25% EtOAc:c-Hex, gave 2-chloro-5-iodo-4-methoxypyridine as a white crystalline solid (0.169 g, 0.760 mmol, 22% yield).

1. additionwas added slowly
2. extractionThe aqueous layer was extracted with CH2Cl2 (2×20 mL)
3. washThe organic layers were washed with brine (10 mL)
4. concentrationconcentrated in vacuo onto silica gel
5. customDry flash chromatography
6. washeluting with 25% EtOAc

ORD record

ord-3aa3aeba737e440f8d1960a39c8abeca

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09403797B2