Hydrochloric Acid → 2-(4-Chloro-2-ethynylphenyl)propanenitrile

To a solution of 2-(4-chloro-2-(2-(trimethylsilyl)ethynyl)phenyl)-propanenitrile (0.550 g, 2.1 mmol) in THF (25 mL) was added 5N NaOH (15 mL). After one hour, the reaction was complete as determined by LC-MS and TLC. The solution was acidified with 5N HCl until the pH was about 2. The solution was extracted with EtOAc (3×40 mL). The combined organic layers were washed with water (2×30 mL) and brine (2×30 mL), dried with MgSO4, and concentrated in vacuo. The resulting orange oil was purified using silica flash chromatography on the ISCO with 0-20% EtOAc/hexanes. MS m/e=190 (M+H)+.

1. extractionThe solution was extracted with EtOAc (3×40 mL)
2. washThe combined organic layers were washed with water (2×30 mL) and brine (2×30 mL)
3. dry with materialdried with MgSO4
4. concentrationconcentrated in vacuo
5. customThe resulting orange oil was purified

ORD record

ord-89504feae8b3418c9fc9bf51ec05efc1

Source dataset

uspto-grants-2009_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07635715B2