Iodine → 2-Iodo-4-(trifluoromethyl)phenol

A mixture of iodine (91.6 mmol, 23.2 g) and sodium bicarbonate (91.6 mmol, 7.7 g) was added to a solution of α,α,α-trifluoro-p-cresol (83.3 mmol, 13.5 g) in THF (90 mL) and H2O (90 mL) and the reaction mixture was allowed to stand at room temperature overnight. Sufficient thiourea (5% solution) was added to remove the excess iodine as indicated by the color change of the reaction from deep violet to brown. The reaction mixture was extracted with ether (3×100 mL), the extract was dried, filtered and the filtrate was concentrated to obtain a brown oil. This oil was distilled (bp 105° C. at 44 mm Hg) to obtain α,α,α-trifluoro-o-iodo-p-cresol (4.1 g, 75% pure, admixed with the starting α,α,α-trifluoro-p-cresol).

1. customto remove the excess iodine
2. customas indicated by the color change of the reaction from deep violet to brown
3. extractionThe reaction mixture was extracted with ether (3×100 mL)
4. customthe extract was dried
5. filtrationfiltered
6. concentrationthe filtrate was concentrated
7. customto obtain a brown oil
8. distillationThis oil was distilled (bp 105° C. at 44 mm Hg)

ORD record

ord-349b421cd8484c9b9f68a0e84c2aedcc

Source dataset

uspto-grants-2009_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07572910B2