Allyl bromide → HCID 14326072, compound

A solution of 3-chlorobenzyl cyanide (2.00 g, 13.2 mmol) in 15 mL of THF was added over 30 min to a suspension of sodium hydride (60% dispersion in mineral oil, 636 mg, 15.9 mmol) in 5.0 mL of dry THF. After stirring 2 h at room temperature, the mixture was cooled to -20 ° C., a solution of allyl bromide (1.14 mL, 1.59 g, 13.2 mmol) in 3.0 mL of THF was added, and the mixture was allowed to warm to room temperature. After 2 h, the reaction was quenched with a solution of 1.6 g of ammonium chloride in 100 mL of water. The aqueous layer was extracted with 3×50 mL of ethyl ether and the combined organic layers were washed with 50 mL of brine, dried over sodium sulfate and concentrated. The residue was purified by flash column chromatography on silica gel, eluting with 20-40% dichloromethane in hexane. Additional purification by flash column chromatography on silica gel, eluting with 5% ethyl ether in hexane gave 897 mg of the title compound as an amber oil. 1NMR (400 MHz, CDCl3): δ 7.36-7.30 (m, 3H), 7.25-7.21 (m, 2H), 5.78 (ddt, 1H, J=17, 10, 7 Hz), 5.21 (bd, 1H, J=10 Hz), 5.20 (dq, 1H, J=17, 1 Hz), 3.84 (t, 1H, J=7 Hz), 2.70-2.57 (m, 2K). Mass spectrum (EI): m/z=191 (M+).

1. temperaturethe mixture was cooled to -20 ° C.
2. temperatureto warm to room temperature
3. waitAfter 2 h
4. customthe reaction was quenched with a solution of 1.6 g of ammonium chloride in 100 mL of water
5. extractionThe aqueous layer was extracted with 3×50 mL of ethyl ether
6. washthe combined organic layers were washed with 50 mL of brine
7. dry with materialdried over sodium sulfate
8. concentrationconcentrated
9. customThe residue was purified by flash column chromatography on silica gel
10. washeluting with 20-40% dichloromethane in hexane
11. customAdditional purification by flash column chromatography on silica gel
12. washeluting with 5% ethyl ether in hexane

ORD record

ord-2e77b6b8f5c54fee9a0d6c1996c1b07f

Source dataset

uspto-grants-1999_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05962462