Acetic Anhydride → N-(4-bromo-3,5-dimethylphenyl)acetamide

HRID 1514875Notes

Reaction equation

HRID 1514875 reaction equation
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([NH2:9])=[CH:4][C:3]=1[CH3:10].[C:11](OC(=O)C)(=[O:13])[CH3:12]>C(Cl)Cl>[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([NH:9][C:11](=[O:13])[CH3:12])=[CH:4][C:3]=1[CH3:10]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 123831174-Bromo-3,5-dimethylaniline

Product 1

HCID 4246250N-(4-bromo-3,5-dimethylphenyl)acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-bromo-3,5-dimethyl-phenylamine (130 mg) in CH2Cl2 (4 mL) was added acetic anhydride (0.123 mL) at 0° C. The mixture was allowed to warm up to room temperature and stirred for 2 h. The mixture was concentrated under reduced pressure. The crude product was purified by column chromatography (SiO2, EtOAc:Hexane=10:90 to 60:40) to give N-(4-bromo-3,5-dimethyl-phenyl)-acetamide: MS (m/z) 244 (M+1); 1H NMR (CDCl3, 400 MHz) δ 7.24 (s, 2H), 2.35 (s, 6H), 2.13 (s, 3H).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customThe crude product was purified by column chromatography (SiO2, EtOAc:Hexane=10:90 to 60:40)

Sources & evidence

ORD record
ord-f20b2d39806543dd80d8ee31b0c9053e
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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