Dimethylamine → 1-[3-bromo-5-(trifluoromethyl)phenyl]-N,N-dimethylmethanamine

To a solution of 3-bromo-5-(trifluoromethyl)benzaldehyde (30 g, 118.6 mmol) in methylene chloride (150 mL) was added dimethylamine (2.0 M in THF, 118 mL) and the reaction was stirred at room temperature for 15 min. The reaction was cooled to 0° C. and sodium triacetoxyborohydride (37.7 g, 178 mmol) was added. The resulting mixture was warmed to room temperature and stirred for 3 h. The solvents were removed under reduced pressure and saturated sodium bicarbonate solution was added. The resulting mixture was extracted three times with ethyl acetate. The combined extracts were washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. Silica gel chromatography (90/10 to 60/40 ethyl acetate/hexanes gradient) provided 1-[3-bromo-5-(trifluoromethyl)phenyl]-N,N-dimethylmethanamine as a colorless oil (Int-8, 24.9 g, 74% yield). LC-MS: (FA) ES+ 282; 1H NMR (300 MHz, CDCl3) δ ppm 7.68 (s, 1H), 7.65 (s, 1H), 7.52 (s, 1H), 3.44 (s, 2H), 2.25 (s, 6H).

1. temperatureThe reaction was cooled to 0° C.
2. temperatureThe resulting mixture was warmed to room temperature
3. stirringstirred for 3 h
4. customThe solvents were removed under reduced pressure and saturated sodium bicarbonate solution
5. additionwas added
6. extractionThe resulting mixture was extracted three times with ethyl acetate
7. washThe combined extracts were washed with brine
8. dry with materialdried over sodium sulfate
9. filtrationfiltered
10. concentrationconcentrated under reduced pressure

ORD record

ord-fab43daa7c1f4aba9155650bb40bd533

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08513421B2