Ammonia → 2-Amino-2-(4-iodophenyl)acetonitrile

To a solution of 4-iodobenzaldehyde (10.4 g) in methanol (36 mL), tetraisopropyl orthotitanate (50.0 mL) and a solution (50 mL) of 8 mol/L ammonia in methanol were added and the mixture was stirred at room temperature for 3.5 hours. Trimethylsilyl cyanide (5.89 mL) was slowly added to the mixture, which was then stirred at the same temperature for 14 hours. Iced water was added to the reaction mixture, which was then filtered through Celite (registered trademark). The filtrate was concentrated under reduced pressure and the resulting residue was extracted with ethyl acetate. The combined organic layers were washed with water and dried over anhydrous magnesium sulfate. The desiccant was removed by filtration and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=99:1-25:75) to give amino(4-iodophenyl)acetonitrile as a pale yellow solid (5.05 g).

1. stirringwas then stirred at the same temperature for 14 hours
2. filtrationwas then filtered through Celite (registered trademark)
3. concentrationThe filtrate was concentrated under reduced pressure
4. extractionthe resulting residue was extracted with ethyl acetate
5. washThe combined organic layers were washed with water
6. dry with materialdried over anhydrous magnesium sulfate
7. customThe desiccant was removed by filtration
8. concentrationthe filtrate was concentrated under reduced pressure
9. customThe resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=99:1-25:75)

ORD record

ord-e3a69db3aa75466abea85074d02c8e6e

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09422240B2