Benzoyl Peroxide → HCID 58138932, compound

Participants

Reaction Steps

In a 500 mL round-bottomed flask N-(4-cyano-2-methylphenyl)-2,2,2-trifluoroacetamide (Intermediate 1; 7.3 g, 32.0 mmol), NBS (5.98 g, 33.6 mmol), and benzoyl peroxide (70%) (1.162 g, 4.80 mmol) were added to carbon tetrachloride (150 mL). The reaction mixture was then heated to reflux under argon for 4 days. The reaction mixture was cooled to room temperature then NBS (0.5 eq, 3 g) and benzoyl peroxide (0.075 eq, 0.581 g) were added. The reaction mixture was then heated to reflux for a further 18 hrs. The reaction mixture was allowed to cool to room temperature then poured into 2M NaOH (100 mL). The organic layer was collected then washed with a solution of sodium metabisulfite (10 g in 100 mL water), dried (MgSO4), filtered and the solvent removed. The resulting orange oil was then purified through a plug of silica gel eluting with 1-10% EtOAc:isoHexane. The desired fractions were then combined and evaporated to dryness to give a 1:1 mixture of the title compound and the starting material as an orange solid (9 g) which was then used in the next step without further purification.

Provenance & Evidence