Acetic Anhydride → N-(4-fluoro-2-(trifluoromethyl)phenyl)acetamide
Reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([C:9]([F:12])([F:11])[F:10])[CH:3]=1.[C:13](OC(=O)C)(=[O:15])[CH3:14]>>[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:13](=[O:15])[CH3:14])=[C:4]([C:9]([F:10])([F:11])[F:12])[CH:3]=1Participants
Procedure
A solution of 4-fluoro-2-(trifluoromethyl)aniline (5.0 g, 27.91 mmol) in acetic anhydride (25 mL) was stirred at ambient temperature for 3 hours to produce a white needle precipitate. The reaction mixture was poured onto ice water, filtered then dried to give 6.0 g of N-[4-fluoro-2-(trifluoromethyl)phenyl]acetamide as an off-white solid which was used without further purification. The N-[4-fluoro-2-(trifluoromethyl)phenyl]acetamide (2.0 g, 9.04 mmol) was dissolved in concentrated H2SO4 (15 mL) and cooled to 0 degrees Centigrade using an ice bath. 70% HNO3 (1.5 mL) was added drop wise and the reaction stirred at 0 degrees Centigrade for 30 min and then at ambient temperature for 3 hours. The reaction mixture was poured onto ice-water, filtered then dried to give 2.4 g of the desired N-[4-fluoro-2-nitro-6-(trifluoromethyl)phenyl]acetamide.
Workup
- customto produce a white needle precipitate
- additionThe reaction mixture was poured onto ice water
- filtrationfiltered
- customthen dried
Sources & evidence
- ORD record
- ord-eb45ae6b1d9545c59898651f869b26a6
- Source dataset
- uspto-grants-2011_05
- Patent number
- US07939528B2
Reaction notes
Loading…