1,2-Dibromoethane → 1-(3-Methoxyphenyl)cyclopropane-1-carbonitrile

To a mixture of 2-(3-methoxyphenyl)acetonitrile (100 mg, 0.679 mmol), 1,2-dibromoethane (88 μL, 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×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, CDCl3) 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, 1H).

1. washwashed with water (0.5 mL×2) and brine (0.5 mL)
2. dry with materialThe organics were dried over magnesium sulfate
3. filtrationfiltered
4. concentrationconcentrated under reduced pressure
5. customdried under high vacuum
6. customThe residue was purified via flash chromatography (0-60% ethyl acetate in heptanes)

ORD record

ord-2c30b0e3674f41bea8535b2641703f05

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09296745B2