Acetic Anhydride → 2-Acetamido-4-fluorotoluene

HRID 227714Notes

Reaction equation

HRID 227714 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:9])=[C:6]([CH:8]=1)[NH2:7].[C:10](OC(=O)C)(=[O:12])[CH3:11]>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:9])=[C:6]([NH:7][C:10](=[O:12])[CH3:11])[CH:8]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 677745-Fluoro-o-toluidine

Product 1

HCID 35231182-Acetamido-4-fluorotolueneYield 82%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

5-Fluoro-2-methylaniline (10.0 g, 79.9 mmol, 1 equiv) was dissolved In toluene (50 mL) and placed in a cool water bath. Acetic anhydride (11.3 mL, 120 mmol, 1.5 equiv) was added slowly. After 15 minutes, a white precipitate had formed. The solid was collected by filtration and washed with toluene several times, affording 10.93 g (82%) of the title compound as a white crystalline solid. MS (ES+) m/e 213 [M+H].

Workup

  1. customplaced in a cool water bath
  2. customa white precipitate had formed
  3. filtrationThe solid was collected by filtration
  4. washwashed with toluene several times

Sources & evidence

ORD record
ord-ba22637887ac4a49983b482361708f69
Source dataset
uspto-grants-2009_07
Patent number
US07560467B2

Reaction notes

Loading…