Acetic Anhydride → 2'-Bromoacetanilide

HRID 2224298Notes

Reaction equation

HRID 2224298 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[C:9](OC(=O)C)(=[O:11])[CH3:10]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[Br:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH:4][C:9](=[O:11])[CH3:10]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 119922-Bromoaniline

Product 1

HCID 1364162'-Bromoacetanilide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 2-bromoaniline (22.0 g, 12.8 mmol), acetic anhydride (13.06 g, 12.8 mmol) and a catalytic amount of DMAP in CH2Cl2 (100 mL) was stirred at 0° C. The mixture was slowly warmed to room temperature and stirred overnight. The reaction mixture was washed with saturated aqueous NaHCO3 solution and concentrated. The residue was triturated with hexanes/CH2Cl2, the solid was filtered and rinsed with hexanes to give aa (25.4 g, 92.8%). HPLC Rt=1.523 min.

Workup

  1. washThe reaction mixture was washed with saturated aqueous NaHCO3 solution
  2. concentrationconcentrated
  3. customThe residue was triturated with hexanes/CH2Cl2
  4. filtrationthe solid was filtered
  5. washrinsed with hexanes
  6. customto give aa (25.4 g, 92.8%)

Sources & evidence

ORD record
ord-f7d31d40a2d3432188a4bfee150aacd1
Source dataset
uspto-grants-2008_05
Patent number
US07378426B2

Reaction notes

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