Iodine → 1-Iodo-3-methoxy-5-(trifluoromethyl)benzene

Temperatur

50 °C

3-methoxy-5-(trifluoromethyl)aniline (100 mg, 0.52 mmol) was dissolved in CHCl3 (5.2 mL) and t-butyl nitrite (124 μL, 1.05 mmol) was added dropwise by syringe. Iodine (266 mg, 1.05 mmol) was added and then the reaction was slowly heated to 50° C. and was maintained at this temperature for an hour and thirty minutes. The reaction was then cooled to room temperature and poured into aq. NaHSO3 (50 mL). The mixture was extracted with EtOAc (50 mL) and the organic extracts were washed with aq. NaHSO3 (3×50 mL) and brine (20 mL), dried over Na2SO4, filtered, and concentrated. Purification by flash chromatography with 1% to 15% EtOAc/hexanes afforded 1-iodo-3-methoxy-5-(trifluoromethyl)benzene. Rf=0.75 (25% EtOAc/hexanes). 1H NMR (CDCl3, 500 MHz) δ 7.53 (s, 1H), 7.41 (s, 1H), 7.09 (s, 1H), 3.82 (s, 3H).

1. temperaturewas maintained at this temperature for an hour and thirty minutes
2. temperatureThe reaction was then cooled to room temperature
3. extractionThe mixture was extracted with EtOAc (50 mL)
4. washthe organic extracts were washed with aq. NaHSO3 (3×50 mL) and brine (20 mL)
5. dry with materialdried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated
8. customPurification by flash chromatography with 1% to 15% EtOAc/hexanes

ORD-Eintrag

ord-af5aad6c0b7141c09bdc994dbba30573

Quelldatensatz

uspto-grants-2010_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07737295B2