Sulfuric Acid → 2-Iodo-4-(trifluoromethyl)phenol

Temperatur

0 °C

N-iodosuccinimide (69.5 g, 0.309 moles) was suspended in acetic acid (257 mL) and cooled to 0° C. 4-Trifluoromethylphenol (50.0 g, 0.310 moles) was added followed by sulphuric acid (5.44 mL) dropwise over 5 minutes. The orange-brown suspension was stirred whist warming slowly to room temperature over 18 hours. A further portion of N-iodosuccinimide (2.5 g, 0.011 moles) was added and the mixture was stirred at room temperature for 24 hours. The reaction was quenched by adding water (150 mL) and extracted with dichloromethane (2×100 mL). The combined organics were washed with a saturated aqueous solution of sodium metabisulphite (2×50 mL) and then with saturated aqueous sodium chloride solution (50 mL). The organics were dried over anhydrous magnesium sulphate, filtered and the solvents removed in vacuo to give the crude title product as a light yellow oil. This batch was combined with the products from two further identical reactions and purified by distillation in vacuo. The product was collected boiling at approximately 45° C. at 2 mBar to give the title compound as a pink-orange semi-solid (216 g).

1. temperaturewarming slowly to room temperature over 18 hours
2. stirringthe mixture was stirred at room temperature for 24 hours
3. customThe reaction was quenched
4. additionby adding water (150 mL)
5. extractionextracted with dichloromethane (2×100 mL)
6. washThe combined organics were washed with a saturated aqueous solution of sodium metabisulphite (2×50 mL)
7. dry with materialThe organics were dried over anhydrous magnesium sulphate
8. filtrationfiltered
9. customthe solvents removed in vacuo
10. customto give the crude title product as a light yellow oil
11. distillationpurified by distillation in vacuo
12. customThe product was collected boiling at approximately 45° C. at 2 mBar

ORD-Eintrag

ord-4e13e72a21344c4f9c57a1d93514f927

Quelldatensatz

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08541588B2