Acetic Anhydride → N-(4-Bromo-5-fluoro-2-methylphenyl)acetamide

HRID 1396681Notes

Reaction equation

HRID 1396681 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:9])=[C:6]([CH:8]=1)[NH2:7].[C:10]([O:13]C(=O)C)(=O)[CH3:11].[Br:17]Br>C1(C)C=CC=CC=1.C(O)(=O)C.O>[Br:17][C:3]1[C:2]([F:1])=[CH:8][C:6]([NH:7][C:10](=[O:13])[CH3:11])=[C:5]([CH3:9])[CH:4]=1

Participants

7

Reactant 3

HCID 7918Acetic AnhydrideHCID 24408BromineHCID 677745-Fluoro-o-toluidine

Product 1

HCID 23070217N-(4-Bromo-5-fluoro-2-methylphenyl)acetamideYield 87.4%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A solution of 5-fluoro-2-methylaniline (29A, 25 g, 200 mmol) in toluene (250 mL) was treated with acetic anhydride (25 mL, 226 mmol) heated at reflux for 1 hour. The reaction mixture was cooled when a colorless solid precipitated out which was filtered and washed with a mixture of ether and hexanes. The colorless solid was taken in acetic acid (150 mL) and treated dropwise with a solution of bromine (9.6 mL, 186 mmol) in acetic acid (20 mL) and stirred at room temperature for 12 hours. The solution was diluted with water and the solid separating out was filtered and washed to yield N-(4-bromo-5-fluoro-2-methylphenyl)acetamide (29B, 40 g) as a colorless solid.

Workup

  1. temperatureheated
  2. temperatureat reflux for 1 hour
  3. temperatureThe reaction mixture was cooled when a colorless solid
  4. customprecipitated out which
  5. filtrationwas filtered
  6. washwashed with a mixture of ether and hexanes
  7. customthe solid separating out
  8. filtrationwas filtered
  9. washwashed

Sources & evidence

ORD record
ord-dae461ad20cb4dd184311e71810f8ba8
Source dataset
uspto-grants-2014_12
Patent number
US08901139B2

Reaction notes

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