Dimethylformamide → 4-Bromo-2-(trifluoromethoxy)benzaldehyde

Temperature

-70 °C

5-bromo-2-iodophenyl trifluoromethyl ether (500 mg, 1.37 mmol) was dissolved in 10 mL of anhydrous THF and cooled to −70° C. Then, n-butyllithium (0.55 mL of a 2.5 M solution, 1.37 mmol) was added dropwise over the course of 30 minutes. DMF (0.19 mL, 2.74 mmol) was added and the reaction was stirred for 30 minutes at −70° C. and then allowed to warm to 0° C. and stir for three hours. The reaction was quenched with 5 mL of saturated ammonium chloride solution and extracted with ethyl acetate. The organic layer was washed with water, dried over magnesium sulfate, filtered, and concentrated to provide 4-bromo-2-[(trifluoromethyl)oxy]benzaldehyde (100 mg, 0.37 mmol, 27%) as a yellow solid. 1H NMR (400 MHz, DMSO-D6) □ 10.1 (s, 1H), 7.9 (s, 3H)

1. temperatureto warm to 0° C.
2. stirringstir for three hours
3. customThe reaction was quenched with 5 mL of saturated ammonium chloride solution
4. extractionextracted with ethyl acetate
5. washThe organic layer was washed with water
6. dry with materialdried over magnesium sulfate
7. filtrationfiltered
8. concentrationconcentrated

ORD record

ord-fcdb36288fe24876988f32fed359546c

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08173805B2