Réaction #2464167

Équation de réaction

2′,4′-difluoroacetophenone

potassium phosphate

2-[(4-bromophenyl)sulfonyl]benzonitrile

2-cyanobenzenethiol

ammonium chloride

→

title compound

Rendement 56.0%

2-({4-[2-(2,4-difluorophenyl)-2-oxoethyl]phenyl}sulfonyl)benzonitrile

Rendement 56.0%

Solvants

tetrahydrofuran

Conditions de réaction

Traitement

1. 1
   Autreprepared
2. 2
   Extractionthe products extracted into ethyl acetate
3. 3
   SéchageThe organic layer was dried over MgSO4
4. 4
   Concentrationconcentrated in vacuo
5. 5
   AutreDry flash column chromatography
6. 6
   Lavageeluting with 25-40% ethyl acetate/isohexane
7. 7
   Autrefollowed by recrystallisation from ethanol

Mode opératoire

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).

Source