Azobisisobutyronitrile → 2-(Bromomethyl)-4,6-dichlorobenzonitrile

Temperature

78 °C

A solution of 2,4-dichloro-6-methylbenzonitrile (16.9 mmol) in 34 mL chlorobenzene was heated to 50° C. when NBS (18.6 mmol) was added. The flask was purged with Ar before AIBN (1.69 mmol) was added at once still at 50° C. The reaction mixture was then stirred at 78° C. After 2 h and 4 h, another portion of AIBN (1.69 mmol) was added and heating to 78° C. was continued overnight. The solvent was then evaporated off, the resulting residue was redissolved in Et2O and the remaining solid was removed by filtration. The filtrate was washed twice with 2N HCl solution and brine, it was dried over MgSO4 and concentrated in vacuo. Purification with CC (KP-SIL™ from Biotage) using Hept to EtOAc gives the desired compound as yellowish solid.

1. additionwas added
2. additionwas added at once still at 50° C
3. temperatureheating to 78° C.
4. waitwas continued overnight
5. customThe solvent was then evaporated off
6. dissolutionthe resulting residue was redissolved in Et2O
7. customthe remaining solid was removed by filtration
8. washThe filtrate was washed twice with 2N HCl solution and brine, it
9. dry with materialwas dried over MgSO4
10. concentrationconcentrated in vacuo
11. customPurification with CC (KP-SIL™ from Biotage)

ORD record

ord-148fe8e8fe2845a5b253f11f21731bb7

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09409917B2