Ammonium Chloride → HCID 131735769, compound

Temperature

60 °C

To a 100 mL three-necked RBF were added (1-(2,6-dichloro-3-fluorophenyl)-2-nitroethoxy)triethylsilane (3.64 g, 9.88 mmol) in EtOH (16 ml) and water (4 ml) at room temperature followed by addition of iron (5.52 g, 99 mmol) and ammonium chloride (5.29 g, 99 mmol). The flask was purged with nitrogen and was heated to 60° C. under nitrogen for 3 h. The mixture was cooled to room temperature, diluted with 40 mL of MeOH, sonicated for 10 min. Then the solution was decanted through a pad of celite. This process was repeated for three times. The filtrate was concentrated to ˜30 mL and diluted with EtOAc (120 mL). The solid was filtered off and discarded. The filtrate was concentrated under reduced pressure. It was diluted with 50 mL of EtOAc, washed with water, brine, dried over anhydrous MgSO4, and concentrated to give 2-(2,6-dichloro-3-fluorophenyl)-2-((triethylsilyl)oxy)ethanamine hydrochloride as an off-white solid. The HCl salt was dissolved with 50 mL of DCM. The suspension was basicified w/satd aq NaHCO3 (pH=9). The organic layer was separated, washed with brine, dried over anhydrous MgSO4, and concentrated to give 2-(2,6-dichloro-3-fluorophenyl)-2-((triethylsilyl)oxy)ethanamine (2.73 g, 8.07 mmol, 82% yield) as a brown oil. 1H NMR (400 MHz, CDCl3) δ 7.23-7.29 (m, 1H), 6.99-7.06 (m, 1H), 5.35 (dd, J=8.6, 4.9 Hz, 1H), 3.29 (dd, J=13.1, 8.7 Hz, 1H), 2.92 (dd, J=13.2, 4.9 Hz, 1H), 0.83-0.93 (m, 9H), 0.46-0.61 (m, 6H); LCMS: 338.2 [M+H]+.

1. customThe flask was purged with nitrogen
2. temperatureThe mixture was cooled to room temperature
3. additiondiluted with 40 mL of MeOH
4. customsonicated for 10 min
5. customThen the solution was decanted through a pad of celite
6. concentrationThe filtrate was concentrated to ˜30 mL
7. additiondiluted with EtOAc (120 mL)
8. filtrationThe solid was filtered off
9. concentrationThe filtrate was concentrated under reduced pressure
10. additionIt was diluted with 50 mL of EtOAc
11. washwashed with water, brine
12. dry with materialdried over anhydrous MgSO4
13. concentrationconcentrated

ORD record

ord-f505a5c1d46d41c487093b19c960afd7

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09365522B2