2,6-Dichloroaniline → HCID 178512060, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 2,6-dichloroaniline (1.75 g, 10.8 mmol) in toluene (25 mL, anhyd) was added dropwise a 2.0M solution of trimethylaluminum in toluene (8.0 mL, 16 mmol). After 90 min the reaction mixture was charged with a solution of 5-bromothiophene-2-carbonitrile (3.00 g, 16 mmol) in toluene (20 mL, anhyd) and then heated at 90° C. After 5 h the reaction mixture was allowed to cool to ambient temperature and quenched by addition to a stirred slurry of silica (25 g) in 3:1 CHCl3/MeOH (100 mL). After 30 min the resulting mixture was filtered and the solids rinsed with MeOH and DCM. The combined filtrates were concentrated to afford the title compound (3.9 g, quant) as a pale yellow solid, which was used in the next step without purification. GC-MS (EI): 348, 350, 352.

Provenance & Evidence