Isobutyronitrile → HCID 67245760, compound

Temperature

100 °C

2-(3-Ethoxy-phenyl)-2-methyl-propionitrile was prepared using a procedure adapted from literature (Organic Syntheses, Vol. 79, pp. 209-215). To a solution of 1-ethoxy-3-fluoro benzene (3.0 g, 19.4 mmol) in 25 mL of toluene was added solid potassium bis(trimethylsilyl)amide (5.84 g, 29.2 mmol, 1.5 eq) followed by isobutyronitrile (7.08 mL, 77.8 mmol, 4 eq). The reaction mixture was stirred at 100° C. for 12 hr. It was diluted with 75 mL of ethyl acetate and 75 mL of 1N aqueous hydrochloric acid. The layers were separated, and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with water (1×50 mL), brine (1×50 mL), and dried over anhydrous magnesium sulfate. The solids were filtered off, and the filtrate was concentrated in vacuo. The residue was dissolved in 5 mL of methylene chloride and applied to a 40 g silica gel cartridge. The product was eluted using a gradient of ethyl acetate in hexanes to yield 2.96 g (15.6 mmol, 80%) of pure 2-(3-ethoxy-phenyl)-2-methyl-propionitrile. LR-MS: 190.12 [(M+H)+]

1. custom2-(3-Ethoxy-phenyl)-2-methyl-propionitrile was prepared
2. customThe layers were separated
3. extractionthe aqueous layer was extracted with ethyl acetate
4. washThe combined organic layers were washed with water (1×50 mL), brine (1×50 mL)
5. dry with materialdried over anhydrous magnesium sulfate
6. filtrationThe solids were filtered off
7. concentrationthe filtrate was concentrated in vacuo
8. dissolutionThe residue was dissolved in 5 mL of methylene chloride
9. washThe product was eluted

ORD record

ord-484685488e8e4e00ac62df505b419992

Source dataset

uspto-grants-2011_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07964724B2