Bromoacetyl bromide → 2-bromo-N-{2-hydroxy-5-[(trifluoromethyl)oxy]phenyl}acetamide

Temperatur

0 °C

2-amino-4-[(trifluoromethyl)oxy]phenol (3.0 g, 15.5 mmol) was dissolved in 100 mL of chloroform. 54 mL of saturated sodium bicarbonate solution was added and the new bi-phase mixture was stirred vigorously and cooled to 0° C. using an ice bath. Bromoacetylbromide (2.1 mL, 23.3 mmol) was added drop-wise. Fifteen minutes later the solution was removed from the ice bath and maintained at room temperature for 2 hours before it was determined to be complete by LCMS (two Aquasil C18, 20×1 mm columns were run in sequence, 4 minutes at 0.1 mL/min, 1-99% CH3CN/H2O with 0.018% trifluoroacetic acid, ES) Rt=1.77 min and m/e 314 [M+1]+. The organic layer was separated and the aqueous phase was extracted with 100 mL of chloroform. The combined organic phases were dried over Na2SO4, filtered and concentrated to give 2-bromo-N-{2-hydroxy-5-[(trifluoromethyl)oxy]phenyl}acetamide (4.23 g, 13.5 mmol, 87%) as a brown amorphous solid. MS (ES) m/e 314 [M+H]+.

1. customFifteen minutes later the solution was removed from the ice bath
2. temperaturemaintained at room temperature for 2 hours before it
3. customto be complete by LCMS (two Aquasil C18, 20×1 mm columns were run in sequence, 4 minutes at 0.1 mL/min, 1-99% CH3CN/H2O with 0.018% trifluoroacetic acid, ES) Rt=1.77 min and m/e 314 [M+1]+
4. customThe organic layer was separated
5. extractionthe aqueous phase was extracted with 100 mL of chloroform
6. dry with materialThe combined organic phases were dried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated

ORD-Eintrag

ord-644ebb5458f94b1984b091ab0d9062f2

Quelldatensatz

uspto-grants-2010_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07749998B2