Ammonium Chloride → HCID 21099418, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-[(4-bromophenyl)sulfonyl]benzonitrile (prepared according to the methods of Example 1 Step 1 using 2-cyanobenzenethiol followed by Example 16 Step 1; 0.32 g, 0.993 mmol), 2′,4′-difluoroacetophenone (0.31 g, 1.99 mmol), potassium phosphate (0.48 g, 2.26 mmol), tris(dibenzylideneacetone)dipalladium(0) (9 mg, 0.0098 mmol) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (13 mg, 0.022 mmol) in tetrahydrofuran (1 mL) was degassed then heated at 80° C. under nitrogen for 14 hours. Saturated ammonium chloride solution was added and the products extracted into ethyl acetate. The organic layer was dried over MgSO4 and concentrated in vacuo while loading onto silica. Dry flash column chromatography eluting with 25-40% ethyl acetate/isohexane followed by recrystallisation from ethanol gave the title compound as a beige solid (0.22 g, 56%). δH (500 MHz, CDCl3): 8.33 (1H, d, J=8.0 Hz), 8.05 (2H, d, J=8.3 Hz), 7.95-7.89 (1H, m), 7.83-7.77 (2H, m), 7.70-7.68 (1H, m), 7.43 (2H, d, J=8.3 Hz), 7.00-6.96 (1H, m), 6.92-6.88 (1H, m), 4.33 (2H, d, J=2.7 Hz).

Provenance & Evidence