Bromine → 5-bromo-2-(2,2,2-trifluoroethoxy)benzoic Acid

Temperature

0 °C

To a solution of 2-(2,2,2-trifluoroethoxy)benzoic acid (22 g) in methylene chloride (100 ml), was added AlCl3 (13.3 g) at 0° C.followed by bromine (16.0 g, 0.1 mol). The reaction mixture was stirred at 0° C. for 1 hour and then at reflux for 2 hours. The solids were filtered and water (50 ml) and ethyl acetate (50 ml) were added to the filtrate. The aqueous layer was separated and extracted with ethyl acetate (2×60 ml) and the combined organic layers were washed with water (2×60 ml). The organic layer was concentrated under vacuum to dryness and hexane (100 ml) was added and the resulting suspension was stirred at 20 to 25° C. for 1 hour. The mixture was filtered and the cake was rinsed with heptanes (2×20 ml). The damp solids were dried in vacuum at 45° C. for 5–6 hours to give a white solid (28.3 g, yield 94.6%), m.p. 126–128° C.

1. temperatureat reflux for 2 hours
2. filtrationThe solids were filtered
3. additionwater (50 ml) and ethyl acetate (50 ml) were added to the filtrate
4. customThe aqueous layer was separated
5. extractionextracted with ethyl acetate (2×60 ml)
6. washthe combined organic layers were washed with water (2×60 ml)
7. concentrationThe organic layer was concentrated under vacuum to dryness and hexane (100 ml)
8. additionwas added
9. stirringthe resulting suspension was stirred at 20 to 25° C. for 1 hour
10. filtrationThe mixture was filtered
11. washthe cake was rinsed with heptanes (2×20 ml)
12. customThe damp solids were dried in vacuum at 45° C. for 5–6 hours

ORD record

ord-fc49323d44494d8f916a028976a9362a

Source dataset

uspto-grants-2007_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07196197B2