Ammonium Chloride → HCID 10264208, compound

1-Bromo-2-fluorobenzene (15 g) and 4-[(2S)-2-(3,4,5,6-tetrahydro-2H-pyran-2-yloxy)propionyl]morpholine (40 g) were dissolved in tetrahydrofuran (200 ml), to which magnesium (turnings: 4.4 g) was added. The mixture was stirred vigorously. The reaction flask was cooled when the temperature of the reaction solution reached to 35° C., and 1-bromo-2-fluorobenzene (16.7 g) was added thereto over the period of 10 minutes while the temperature of the reaction solution was kept at 35 to 37° C. After the reaction solution was stirred at 30 to 35° C. for 2 hours, it was cooled in an icebath. A saturated aqueous solution of ammonium chloride (100 ml) was added thereto and the mixture was extracted with ethyl acetate (200 ml×2,100 ml). The extract was washed with water and a saturated aqueous solution of sodium chloride successively, dried over anhydrous magnesium sulfate, and distilled under reduced pressure to remove the solvent. The residue was subjected to silica gel chromatography (eluent: hexane/ethyl acetate=10/1 to 5/1) to give (2S)-2′-fluoro-2-(3,4,5,6-tetrahydro-2H-pyran-2-yloxy)-propiophenone (22.4 g) as a pale yellow oily substance.

1. additionwas added
2. temperatureThe reaction flask was cooled when the temperature of the reaction solution
3. customreached to 35° C.
4. customover the period of 10 minutes
5. customwas kept at 35 to 37° C
6. stirringAfter the reaction solution was stirred at 30 to 35° C. for 2 hours
7. temperatureit was cooled in an icebath
8. extractionthe mixture was extracted with ethyl acetate (200 ml×2,100 ml)
9. washThe extract was washed with water
10. dry with materiala saturated aqueous solution of sodium chloride successively, dried over anhydrous magnesium sulfate
11. distillationdistilled under reduced pressure
12. customto remove the solvent

ORD record

ord-355bb9b9a3134f3d85e074b8d9ace153

Source dataset

uspto-grants-2002_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06362206B1