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

HRID 53787Notes

Reaction equation

HRID 53787 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): δ 2.184 (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-c25ef26b833d4b2b9a9f5226d7c28687
Source dataset
uspto-grants-1997_04
Patent number
US05620979

Reaction notes

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