Acetic Acid → 3-METHYL-4-BROMOACETANILIDE

HRID 1405063Notes

Reaction equation

HRID 1405063 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[CH3:9].[C:10](O)(=[O:12])[CH3:11].C(OC(=O)C)(=O)C>>[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:10](=[O:12])[CH3:11])=[CH:4][C:3]=1[CH3:9]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 7918Acetic AnhydrideHCID 233594-Bromo-3-methylaniline

Product 1

HCID 7383363-METHYL-4-BROMOACETANILIDEYield 94%

Procedure

To a stirring solution of 4-bromo-3-methylaniline (4.3 g, 23.11 mmol) in acetic acid (2 mL, 23.11 mmol) at room temperature was added acetic anhydride (2.62 mL, 27.7 mmol). The reaction mixture was refluxed for 30 min, cooled to room temperature and then poured into 20 mL of ice water while allowing to stir for 5 min. The aqueous suspension was filtered, and the solid was washed with water, dissolved in CH2Cl2 and then dried over sodium sulfate. The organic layer was filtered and concentrated under reduced pressure to yield Intermediate 1B (4.96 g, 21.73 mmol, 94% yield) as an off-white solid. MS (ES): m/z=229.9 [M+H]+.

Workup

  1. temperatureThe reaction mixture was refluxed for 30 min
  2. filtrationThe aqueous suspension was filtered
  3. washthe solid was washed with water
  4. dissolutiondissolved in CH2Cl2
  5. dry with materialdried over sodium sulfate
  6. filtrationThe organic layer was filtered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-efee5497b31e40dcae600d64ccab38f5
Source dataset
uspto-grants-2014_12
Patent number
US08916553B2

Reaction notes

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