Hydrochloric Acid → HCID 69001066, compound

Temperature

-78 °C

To a solution of N-(4-chloro-2-fluorophenyl)acetamide (10.0 g, 53.3 mmol) and diisopropylamine (7.5 mL, 53.3 mmol) in THF (300 mL) at −78° C. is added dropwise n-BuLi (2.5 M in hexanes, 42.6 mL, 106.6 mmol) keeping the reaction temperature below −60° C. After 2 hours, iodoethane (12.4 g, 80 mmol) is added dropwise at −78° C. The reaction mixture is stirred at −78° C. for additional 1.5 hours. A 1N solution of aqueous HCl is added slowly until a pH between 4 and 5 is reached. The mixture is extracted with EtOAc (200 mL×3) and the organic layers are combined washed with water and brine, then dried over MgSO4. The solvent is removed under reduced pressure and the solid residue is stirred in ether and hexane (1:4, 80 mL) for 1 hour. The filtered solid is dried to give N-(4-chloro-3-ethyl-2-fluorophenyl)acetamide.

1. customthe reaction temperature below −60° C
2. extractionThe mixture is extracted with EtOAc (200 mL×3)
3. washthe organic layers are combined washed with water and brine
4. dry with materialdried over MgSO4
5. customThe solvent is removed under reduced pressure
6. stirringthe solid residue is stirred in ether
7. waithexane (1:4, 80 mL) for 1 hour
8. customThe filtered solid is dried

ORD record

ord-789ad0605c7d420e908065de43e92292

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08586782B2