Hydrochloric Acid → HCID 68823443, compound

Temperature

-65 °C

To a solution of N-(4-chloro-2-fluorophenyl)acetamide (30.0 g, 147 mmol) in THF (300 mL) at −70° C. is added dropwise (keeping the reaction temperature below −60° C.) n-BuLi (2.0 M in cyclohexane, 147 mL, 294 mmol). The reaction is stirred between −60 to −70° C. for 2 hours and 1,1,1-trifluoro-2-iodoethane (46.2 g, 220 mmol) is added dropwise at −70° C. The reaction mixture is stirred at this temperature for additional 1.5 hours before 3N HCl (108 mL) solution is added slowly. The mixture is allowed to warm up to room temperature and extracted with EtOAc (200 mL×3). The organic layers are combined washed with water, brine and then dried over MgSO4. The solvents are removed and the residue is stirred in ether and hexanes (1:2, 120 mL) for 1 hour. A solid precipitate is filtered to give N-(2,4-dichloro-3-iodophenyl)acetamide.

1. customthe reaction temperature below −60° C.
2. additionis added slowly
3. temperatureto warm up to room temperature
4. extractionextracted with EtOAc (200 mL×3)
5. washThe organic layers are combined washed with water, brine
6. dry with materialdried over MgSO4
7. customThe solvents are removed
8. stirringthe residue is stirred in ether
9. waithexanes (1:2, 120 mL) for 1 hour
10. filtrationA solid precipitate is filtered

ORD record

ord-7f661addbf68476d9e815e15b3716002

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08586782B2