Ammonia → 3-(3-Bromo-4-fluorophenyl)propanimidamide hydrochloride

To a solution of 3-(3-bromo-4-fluorophenyl)propanenitrile (5.0 g, 21.05 mmol) in toluene (20 mL) and methanol (6.32 mL, 156 mmol) at 0° C. was added acetyl chloride (7.51 mL, 105 mmol) dropwise over 5 min. The reaction mixture was allowed to warm to room temperature and stirred for 2 h. The mixture was cooled to 0° C. by an ice bath, to which ammonia (30.1 mL, 210 mmol) was added dropwise. The reaction mixture was stirred at room temperature overnight. The mixture was filtered, and the filtrate was concentrated to give a crude product. Recrystallization from toluene/methanol (1:1) then afforded the title compound as a white solid (5.2 g, 93% yield). LCMS: rt=1.18 min, [M+H+]=245

1. additionwas added dropwise
2. stirringThe reaction mixture was stirred at room temperature overnight
3. filtrationThe mixture was filtered
4. concentrationthe filtrate was concentrated
5. customto give a crude product
6. customRecrystallization from toluene/methanol (1:1)

ORD record

ord-c466bac0dd324917b99b21f04c248937

Source dataset

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08637536B2