Potassium Carbonate → HCID 66678677, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 4-methyl-2-chlorobenzonitrile (1.51 g, 10 mmol), N-bromosuccinimide (2.14 g, 12.0 mmol) and AIBN (33 mg, 0.20 mmol) in ACN (40 mL) was heated under reflux for 18 hours. The reaction mixture was diluted with EtOAc and washed with a saturated aqueous solution of Na2CO3 and brine. The organic layer was dried (MgSO4) and concentrated under vacuum. The residue was treated with sarcosine tert-butyl ester hydrochloride (1.44 g, 7.92 mmol) and K2CO3 (2.74 g, 19.8 mmol) in ACN (10 mL). The mixture was heated at 100° C. for 2 hours. The solvent was evaporated under vacuum. The residue was dissolved in a mixture of DCM and water and then poured through a hydrophobic frit. The solvent was evaporated under vacuum. The residue was purified by flash chromatography (silica, iso-hexane/Et2O) to afford the title compound (1.95 g, quantitative). 1H NMR (CDCl3, 400 MHz) δ 7.61 (1H, d, J=8.0 Hz), 7.57 (1H, s), 7.36 (1H, m), 3.73 (2H, s), 3.21 (2H, s), 2.36 (3H, s), 1.48 (9H, s).

Provenance & Evidence