Chlorosuccinimide → 1-(3-Chloroprop-2-ynyloxy)-2-(trifluoromethoxy)benzene

To a solution of the product of Example 6A (13.0 g, 56.1 mmol) in acetone (200 mL) was added N-chlorosuccinimide (8.99 g, 67.3 mmol) and silver acetate (0.936 g, 5.61 mmol). The reaction mixture was heated at reflux for 16 hours, cooled to ambient temperature, and the solvent removed under reduced pressure. The residue was taken up in a mixture of diethyl ether and water, and filtered to remove the silver salts. The filtrate was extracted with diethyl ether (300 mL). The combined organic layers were washed with saturated sodium bicarbonate (75 mL) and concentrated to give the title compound (12.9 g) which was used without further purification in the next step. MS (DCI) m/z 268 (M+NH4)+.

1. temperatureThe reaction mixture was heated
2. temperatureat reflux for 16 hours
3. customthe solvent removed under reduced pressure
4. additionThe residue was taken up in a mixture of diethyl ether and water
5. filtrationfiltered
6. customto remove the silver salts
7. extractionThe filtrate was extracted with diethyl ether (300 mL)
8. washThe combined organic layers were washed with saturated sodium bicarbonate (75 mL)
9. concentrationconcentrated

ORD record

ord-0ac55f3b11d94d1bb04fd9c79d2f9193

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08859584B2