Acetic Anhydride → N-(2-bromo-4-chlorophenyl)acetamide

HRID 2220205Notes

Reaction equation

HRID 2220205 reaction equation
[Br:1][C:2]1[CH:8]=[C:7]([Cl:9])[CH:6]=[CH:5][C:3]=1[NH2:4].[C:10](OC(=O)C)(=[O:12])[CH3:11]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[Br:1][C:2]1[CH:8]=[C:7]([Cl:9])[CH:6]=[CH:5][C:3]=1[NH:4][C:10](=[O:12])[CH3:11]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 701102-Bromo-4-chloroaniline

Product 1

HCID 282685N-(2-bromo-4-chlorophenyl)acetamideYield 87.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of 2-bromo-4-chloroaniline (5 g, 24 mmol) and catalytic DMAP in CH2Cl2 (15 mL) was add acetic anhydride (2.3 mL, 24 mmol) at room temperature. The reaction mixture was stirred overnight then washed with saturated aqueous NaHCO3 solution. The CH2Cl2 layer was dried (MgSO4), filtered, concentrated in vacuo. The crude material was triturated with Hexane/Et2O and the solid filtered and dried in vacuo to give N-(2-bromo-4-chloro-phenyl)-acetamide (5.2 g, 86%). HPLC: Rt=2.26 min. m/z=248 (M+H+).

Workup

  1. washthen washed with saturated aqueous NaHCO3 solution
  2. dry with materialThe CH2Cl2 layer was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude material was triturated with Hexane/Et2O
  6. filtrationthe solid filtered
  7. customdried in vacuo

Sources & evidence

ORD record
ord-85e1242276624c748c3f16f9b3a8a6b9
Source dataset
uspto-grants-2008_08
Patent number
US07417040B2

Reaction notes

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