Iodine → 4-Chloro-2-iodophenol

To a solution of 4-chlorophenol in THF (75 mL), and H2O (75 mL) was added a mixture of crushed iodine (78.7 mmol, 20 g) and sodium bicarbonate (78.7 mmol, 6.6 g). The reaction mixture was stirred at room temperature overnight, then quenched with sufficient 5% sodium thiosulfate solution to turn the color of the reaction mixture from deep violet to light yellow and extracted with ether (2×200 mL). The ether layer was collected, washed with H2O, and the washed ether layer was dried, filtered and the filtrate was evaporated to a crude product, which was purified by distillation to obtain 4-chloro-2-iodo phenol (7%,1.3 g); mp 79° C.-82° C.

1. customquenched with sufficient 5% sodium thiosulfate solution
2. extractionextracted with ether (2×200 mL)
3. customThe ether layer was collected
4. washwashed with H2O
5. dry with materialthe washed ether layer was dried
6. filtrationfiltered
7. customthe filtrate was evaporated to a crude product, which
8. distillationwas purified by distillation

ORD record

ord-26702e844a7e4005b8c3f92165c0e4d3

Source dataset

uspto-grants-2003_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06579879B2