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

Temperature

78 °C

A soln. 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 conc. in vacuo. Purification with CC (0-100% EtOAc/Hept) 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 and conc. in vacuo
10. customPurification with CC (0-100% EtOAc/Hept)

ORD record

ord-3e91f654cc15416fa94d1c59339f3fbd

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09388197B2