Azobisisobutyronitrile → 3-(Bromomethyl)-5-fluorobenzonitrile

Temperature

70 °C

3-Fluoro-5-methylbenzonitrile (Hognda Trading; 100 g, 0.74 mol) was taken in acetonitrile (1 L) at 25° C. under nitrogen atmosphere. N-Bromosuccinimide (105 g, 0.59 mol) and AIBN (2.4 g, 0.014 mol) were added and the reaction mixture was heated at 70° C. for 1 h 20 minutes. The reaction mixture was cooled to 25° C. and concentrated. The residue was diluted, cooled to 0-5° C. and stirred for 15 minutes at the same temperature. The precipitated succinimide was filtered and the filtrate was concentrated to get crude product as yellow oil (90 g). It was taken in petroleum ether (200 mL) and cooled to −20° C. stirred for 30 minutes. The precipitated solids were filtered and dried to get the title product as white solid. 1H NMR (DMSO-d6; 400 MHz): δ 7.83 (m, 2H), 7.73 (m, 1H), 4.72 (s, 2H). HPLC (Method A) Rt: 4.17 min (Purity: 99.4%).

1. temperatureThe reaction mixture was cooled to 25° C.
2. concentrationconcentrated
3. additionThe residue was diluted
4. temperaturecooled to 0-5° C.
5. filtrationThe precipitated succinimide was filtered
6. concentrationthe filtrate was concentrated
7. customto get crude product as yellow oil (90 g)
8. temperaturecooled to −20° C.
9. stirringstirred for 30 minutes
10. filtrationThe precipitated solids were filtered
11. customdried

ORD record

ord-f45ca2caf7854056af437cc9a310816c

Source dataset

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09029405B2