1-(3-METHOXYPHENYL)CYCLOPROPANECARBONITRILE synthesis
- Product Name:1-(3-METHOXYPHENYL)CYCLOPROPANECARBONITRILE
- CAS Number:74205-01-9
- Molecular formula:C11H11NO
- Molecular Weight:173.21
Yield:74205-01-9 48%
Reaction Conditions:
with tetrabutylammomium bromide;sodium hydroxide in water;toluene at 20; for 16 h;
Steps:
1 Step 1 : 1 -(3-Methoxyphenyl)cyclopropanecarbonitrile
Step 1 : 1 -(3-Methoxyphenyl)cyclopropanecarbonitrile To a mixture of 2-(3-methoxyphenyl)acetonitrile (100 mg, 0.679 mmol), 1 ,2- dibromoethane (88 μΙ_, 1.02 mmol) and tetrabutylammonium bromide (50 mg, 0.16 mmol) in toluene (1.0 mL) was added an aqueous solution of sodium hydroxide (50%, 500 mg in 0.5 mL of water, 12.5 mmol) at room temperature. The reaction mixture was stirred at room temperature for 16 h. The reaction mixture was diluted with ethyl acetate (2 mL) and washed with water (0.5 mL x 2) and brine (0.5 mL). The organics were dried over magnesium sulfate, filtered, concentrated under reduced pressure and dried under high vacuum. The residue was purified via flash chromatography (0-60% ethyl acetate in heptanes) to afford 1-(3-methoxyphenyl)cyclopropanecarbonitrile as an oil (56 mg, 48%). 1H NMR (500 MHz, CDCI3) δ 1 .38-1 .44 (m, 2H), 1.69-1.76 (m, 2H), 3.83 (s, 3H), 6.74-6.96 (m, 3H), 7.22-7.31 (m, 1 H).
References:
WO2013/150416,2013,A1 Location in patent:Page/Page column 78; 79
