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

To a solution of the product of Example 66A (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 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 (12.85 g) which was used without further purification in the next step. 1H NMR (300 MHz, CDCl3) δ 7.30-7.24 (m, 2H), 7.15-7.09 (m, 1H), 7.01 (td, J=7.8, 1.4 Hz, 1H), 4.77 (s, 2H); MS (DCI) m/z 268 (M+NH4)+.

1. temperatureThe reaction 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-93ac8135998441e6970905bc6819af47

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08604053B2