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

HRID 54375

Reaction equation

HRID 54375 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-890b39580f944ef89398cbf59463adc2
Source dataset
uspto-grants-1997_04
Patent number
US05622952

Linked notes

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