Acetic Anhydride → N-[4-Bromo-2-fluoro-5-(trifluoromethyl)phenyl]acetamide

HRID 1504943Notes

Reaction equation

HRID 1504943 reaction equation
[Br:1][C:2]1[C:8]([C:9]([F:12])([F:11])[F:10])=[CH:7][C:5]([NH2:6])=[C:4]([F:13])[CH:3]=1.[C:14](OC(=O)C)(=[O:16])[CH3:15]>N1C=CC=CC=1>[Br:1][C:2]1[C:8]([C:9]([F:10])([F:11])[F:12])=[CH:7][C:5]([NH:6][C:14](=[O:16])[CH3:15])=[C:4]([F:13])[CH:3]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 70180464-Bromo-2-fluoro-5-(trifluoromethyl)aniline

Product 1

HCID 23274446N-[4-Bromo-2-fluoro-5-(trifluoromethyl)phenyl]acetamideYield 83%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of compound 22 (3.6 g, 14 mmol), acetic anhydride (8 mL) and pyridine (0.1 mL) was stirred at room temperature for 1 h, then concentrated in vacuo. The residue was added ice and sodium bicarbonate (until pH=7). The resulted mixture was extracted with EtOAc. The organic layers were combined, washed by brine, dried over Na2SO4, filtered and concentrated to give the title compound 23 (3.5 g, 83%). 1H NMR (400 MHz, CDCl3) δ8.79 (d, 1H, J=7.8 Hz), 7.46 (d, 1H, J=10.0 Hz), 7.38 (br s, 1H), 2.24 (s, 3H).

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe residue was added ice and sodium bicarbonate (until pH=7)
  3. extractionThe resulted mixture was extracted with EtOAc
  4. washwashed by brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-2db1ba29aff14a2cbaa47ab2a7b3323c
Source dataset
uspto-grants-2015_12
Patent number
US09216957B2

Reaction notes

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