Acetic Acid → (5-Bromo-2-iodo-benzyl)-ethyl-amine

To 5-bromo-2-iodo-benzaldehyde (15.0 g, 48.3 mmol) in methanol (60 mL) was added ethylamine (2.0M in methanol; 48 mL, 72.0 mmol), followed by acetic acid (3.0 mL, 53.4 mmol), and the mixture was stirred at room temperature for 30 minutes, after which a precipitate formed. Sodium cyanoborohydride (6.00 g, 95.4 mmol) was then added in 3 portions and the precipitate disappeared. The reaction was stirred at room temperature for 24 hours then quenched with saturated aqueous sodium bicarbonate. The resulting mixture was evaporated then diluted with dichloromethane and washed with water, dried over magnesium sulfate, filtered, and concentrated. The residue was purified by silica gel chromatography (0-4% methanol in dichloromethane) to give the title compound.

1. customafter which a precipitate formed
2. stirringThe reaction was stirred at room temperature for 24 hours
3. customthen quenched with saturated aqueous sodium bicarbonate
4. customThe resulting mixture was evaporated
5. additionthen diluted with dichloromethane
6. washwashed with water
7. dry with materialdried over magnesium sulfate
8. filtrationfiltered
9. concentrationconcentrated
10. customThe residue was purified by silica gel chromatography (0-4% methanol in dichloromethane)

ORD record

ord-5f82fe486a71488e898637325541a050

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08785393B2