5-Norbornene-2-carbonitrile synthesis
- Product Name:5-Norbornene-2-carbonitrile
- CAS Number:95-11-4
- Molecular formula:C8H9N
- Molecular Weight:119.16
67403-76-3
121-46-0
2436-90-0
95-11-4
The general procedure for the synthesis of 3,7-dimethylocta-1,6-diene and bicyclo[2.2.1]hept-5-ene-2-carbonitrile from the compound (CAS:67403-76-3) and dicycloheptadiene was as follows: to a 4 mL screw-capped vial in an argon-protected glove box were added sequentially the compound 69 (82.6 mg, 0.50 mmol), norepiglottidiene 8 (51 μL, 0.5 mmol), hexane solution of 1.0 M AIMe2Cl (50 μL, 10.0 mol%, 0.05 mmol), Ni(COD)2 (3.45 mg, 2.5 mol%, 12.5 μmol), and DPEphos (6.75 mg, 2.5 mol%, 12.5 μmol) in THF ( 1.0 mL) solution. The vials were removed from the glove box and the reaction temperature was controlled at 28°C. The reaction mixture was stirred at 28 °C for 16 h and then concentrated under reduced pressure. The residue was purified by silica gel fast column chromatography (100% pentane as eluent) to afford product 70 (49.0 mg, 71% yield). The structure of the product was confirmed by 1H NMR (500 MHz, CDCl3) and 13C NMR (125 MHz, CDCl3) as follows: 1H NMR δ 5.74-5.64 (m, 1H), 5.13-5.06 (m, 1H), 4.99-4.88 (m, 2H), 2.12 (p, J=7.0 Hz, 1H ), 2.01-1.89 (m, 2H), 1.68 (s, 3H), 1.60 (s, 3H), 1.35-1.26 (m, 2H), 0.99 (d, J=6.9Hz, 3H); 13C NMR δ 144.91, 131.44, 124.80, 112.61, 37.51, 36.89, 25.88, 20.30, 17.83.
Yield:95-11-4 97%
Reaction Conditions:
with methyl bicyclononadiene at 190; for 800 h;
Steps:
1 Comparative Example 1
As a result, an average yield of the obtained cyanonorbornene was 90% based on cyclopentadiene obtained by decomposition of dicyclopentadiene of a raw material, after 12 hours of starting of operation.
In addition, regarding the reaction product, an amount of methyl bicyclononadiene was 0.02% by weight with respect to a total amount of 100% by weight of cyanonorbornene, methyl bicyclononadiene, and a non-reactive raw material (dicyclopentadiene and acrylonitrile).
References:
US2020/239408,2020,A1 Location in patent:Paragraph 00148-0149
![Bicyclo[2.2.1]hept-5-ene-2-carboxaldehyde, oxime, [1α,2β(Z),4α]- (9CI)](/CAS/20210305/GIF/96193-44-1.gif)
96193-44-1
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