Ammonia → HCID 68712687, compound

To a stirred solution of 4-fluoro-2-(trifluoromethyl)benzaldehyde (5.0 g) in methanol (20 ml) were added sequentially ammonia solution (28.9 ml, 7 M solution in methanol) and tetraisopropyl orthotitanate (9.0 ml) and the resulting mixture was stirred at r.t. for 1 h. Trimethylsilylcyanide (3.3 ml) was then added dropwise and stirring continued at r.t. overnight. The reaction mixture was poured onto ice-water (400 ml) and the mixture was then extracted twice with ethyl acetate. The combined organic phases were washed with brine and then dried over sodium sulphate and concentrated in vacuo to afford (RS)-amino-(4-fluoro-2-trifluoromethyl-phenyl)-acetonitrile (4.48 g, 81%) as an orange viscous oil. MS (ISP): 219.1 ([M+H]+).

1. stirringstirring
2. waitcontinued at r.t. overnight
3. additionThe reaction mixture was poured onto ice-water (400 ml)
4. extractionthe mixture was then extracted twice with ethyl acetate
5. washThe combined organic phases were washed with brine
6. dry with materialdried over sodium sulphate
7. concentrationconcentrated in vacuo

ORD record

ord-f610d3e1128c4c2c975dead96201334c

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08604061B2