Réaction #1256718

Équation de réaction

1-iodo-4-vinyl-benzene

HCl

NaH

malononitrile

→

title compound

Rendement 71.8%

2-(4-vinyl-phenyl)-malononitrile

Rendement 71.8%

Solvants

THF

1,2-dimethoxyethane

1,2-dimethoxyethane

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGthe reaction mixture stirred at 85° C. for 2 h
2. 2
   TempératureAfter cooling to room temperature
3. 3
   workup.ADDITIONthe reaction mixture was poured into ice
4. 4
   Extractionextracted with CH2Cl2 (100 mL)
5. 5
   AutreThe organic layer was separated
6. 6
   Séchagedried over anhydrous Na2SO4
7. 7
   Concentrationconcentrated in vacuo
8. 8
   AutreThe crude product was then purified by flash chromatography on silica gel eluting with 1:1 hexane

Mode opératoire

To an ice-cooled suspension of NaH (0.792 g, 33.0 mmol) in anhydrous 1,2-dimethoxyethane (20 mL) was added dropwise via syringe a solution of malononitrile (0.99 g, 15 mmol) in anhydrous 1,2-dimethoxyethane (5 mL) under N2. The mixture was stirred for 1 h at room temperature under N2. Next, 1-iodo-4-vinyl-benzene (1.15 g, 5.00 mmol), dry THF (15 mL), and tetrakis(triphenyphophine)palladium(0) (0.58g, 0.50 mmol) were added to the resulting pink suspension under an N2 flow, and the reaction mixture stirred at 85° C. for 2 h. After cooling to room temperature, the reaction mixture was poured into ice, neutralized with 10% HCl, and extracted with CH2Cl2 (100 mL). The organic layer was separated, dried over anhydrous Na2SO4, and concentrated in vacuo. The crude product was then purified by flash chromatography on silica gel eluting with 1:1 hexane: CH2Cl2, to give 0.603 g (71.8%) of the title compound as pale yellow solid: mp 40-42° C. ° C; 1H NMR (400 MHz, CDCl3): δ 7.526 (d, 2H, J=7.6 Hz), 7.462 (d, 2H, J=7.6 Hz), 6.738 (d×d, 1H, J1=17.6 Hz, J2=10.8 Hz), 5.846 (d, 1H, J=17.6 Hz), 5.398 (d, 1H, J=10.8 Hz), 5.075 (s, 1H); 13C NMR (100 MHz, CDCl3): δ 139.840, 135.372, 127.766, 127.556, 125.245, 116.619, 111.897, 28.050; Anal. Calcd. for C11H8N2: C, 78.55; H, 4.79; N, 16.66. Found; C, 78.76; H, 4.75; N, 16.02.

Source