Acetic Anhydride → N-(3-Bromo-4-methylphenyl)acetamide

HRID 29819Notes

Reaction equation

HRID 29819 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[CH3:9])[NH2:5].[C:10](OC(=O)C)(=[O:12])[CH3:11]>C(Cl)Cl>[C:10]([NH:5][C:4]1[CH:6]=[CH:7][C:8]([CH3:9])=[C:2]([Br:1])[CH:3]=1)(=[O:12])[CH3:11]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 82187Benzenamine, 3-bromo-4-methyl-

Product 1

HCID 11708413N-(3-Bromo-4-methylphenyl)acetamideYield 99.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-bromo-4-methylaniline (1.27 g, 6.82 mmol) in DCM (20 mL) at (0° C. is added acetic anhydride (0.676 mL, 7.16 mmol) dropwise. After 30 minutes, the mixture is partitioned between DCM and saturated sodium carbonate solution. The layer is separated and the aqueous layer is extracted with DCM. The combined organic extracts are washed with brine, dried over Na2SO4, filtered and concentrated to afford the title compound (1.55 g, 99%). The residue is used in the next step without further purification.

Workup

  1. customthe mixture is partitioned between DCM and saturated sodium carbonate solution
  2. customThe layer is separated
  3. extractionthe aqueous layer is extracted with DCM
  4. washThe combined organic extracts are washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-b205cd67cc5f4963b841b1479888a34a
Source dataset
uspto-grants-2008_09
Patent number
US07423038B2

Reaction notes

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