Acetic Anhydride → Acetamide, N-[4-fluoro-3-(trifluoromethyl)phenyl]-

HRID 439506Notes

Reaction equation

HRID 439506 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:9]([F:12])([F:11])[F:10])[C:5]([F:8])=[CH:6][CH:7]=1.[C:13](OC(=O)C)(=[O:15])[CH3:14]>CCN(CC)CC>[C:13]([NH:1][C:2]1[CH:3]=[C:4]([C:9]([F:12])([F:10])[F:11])[C:5]([F:8])=[CH:6][CH:7]=1)(=[O:15])[CH3:14]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 753774-Fluoro-3-(trifluoromethyl)aniline

Product 1

HCID 10353438Acetamide, N-[4-fluoro-3-(trifluoromethyl)phenyl]-Yield 97%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A solution of 3-amino-6-fluorobenzotrifluoride (2.0 g, 11.17 mmol, Aldrich) in acetic anhydride (10 mL) and Et3N (1 mL) was stirred at room temperature for 24 h, and then most of the acetic anhydride was removed. The white needle crystals were collected by filtration and washed with water (2×2 mL), affording 2.4 g (97%) of 3-acetamido-6-fluorobenzotrifluoride. 1H NMR (CDCl3): δ2.184 (S, 3H); 7.136 (t, 1H, J=9.9 Hz); 7.733 (m, 3H).

Workup

  1. custommost of the acetic anhydride was removed
  2. filtrationThe white needle crystals were collected by filtration
  3. washwashed with water (2×2 mL)

Sources & evidence

ORD record
ord-0afbb6f6aad44483b01e068e359e9e2b
Source dataset
uspto-grants-1996_05
Patent number
US05514680

Reaction notes

Loading…