Acetyl chloride → HCID 67305077, Verbindung

Temperatur

150 °C

To a solution of 4-(2,2,2-trifluoroethyl)phenol (1.00 g, 5.68 mmol) in CH2Cl2 (5.0 ml) was added trifluoromethanesulfonic acid (0.0151 ml, 0.170 mmol) with stirring. A solution of acetic chloride (0.444 ml, 6.25 mmol) in CH2Cl2 (5.0 ml) was added drop wise to the reaction. After stirred 45 min at RT, all the phenol was consumed. The product mixture was diluted with CH2Cl2, washed with saturated sodium bicarbonate. The organic layer was dried over Na2SO4, filtered and concentrated. The residue was dried in vacuum until no weight loss was observed. To the above residue was added anhydrous aluminum(III) chloride (0.757 g, 5.68 mmol). The mixture was heated at 150° C. for 1 h until all the starting material was consumed (monitored by TLC). The resulted brown gum was cooled to 0° C., diluted with diethyl ether and 1N HCl. Layers were separated. The aqueous layer was extracted with ether. The organic layers were combined, dried over Na2SO4, filtered and concentrated. The residue was purified on silica gel column (2-15% EtOAc/hexane) to afford the title compound.

1. customwise to the reaction
2. stirringAfter stirred 45 min at RT
3. customall the phenol was consumed
4. additionThe product mixture was diluted with CH2Cl2
5. washwashed with saturated sodium bicarbonate
6. dry with materialThe organic layer was dried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated
9. customThe residue was dried in vacuum until no weight loss
10. customwas consumed (monitored by TLC)
11. temperatureThe resulted brown gum was cooled to 0° C.
12. additiondiluted with diethyl ether and 1N HCl
13. customLayers were separated
14. extractionThe aqueous layer was extracted with ether
15. dry with materialdried over Na2SO4
16. filtrationfiltered
17. concentrationconcentrated
18. customThe residue was purified on silica gel column (2-15% EtOAc/hexane)

ORD-Eintrag

ord-12e85c5284114715b8efc36c8b079384

Quelldatensatz

uspto-grants-2011_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07973047B2