Ethyl Acetate → 4-Amino-3-bromobenzamide

HRID 1711242Notes

Reaction equation

HRID 1711242 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][CH:3]=1.[Br:11]N1C(=O)CCC1=O.CCOC(C)=O>CC#N.C(Cl)Cl>[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][C:3]=1[Br:11]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 67184N-bromobutanimideHCID 760794-Aminobenzamide

Product 1

HCID 121180554-Amino-3-bromobenzamideYield 92%

Reagents, catalysts & solvents 1

HCID 21877088Acetonitrile methylene chlorideSolvent2×

Procedure

To a suspension of 4-amino-benzamide (1.00 g, 7.34 mmol) in 50 mL of 1:4 CH3CN/DCM at 0° C. was added N-bromosuccinimide (NBS) (1.31 g, 7.34 mmol) in 20 mL of 1:1 CH3CN/DCM. The mixture was warmed to RT and stirred for 16 h under Ar. Treated with 100 mL of EtOAc, the mixture was washed with H2O (2×30 mL), brine (20 mL) and dried (Na2SO4). The organic solvent was evaporated in vacuo and the residue was triturated with DCM to give 1.45 g (92%) of the title compound as a faint yellow solid. Mass spectrum (ESI, m/z): Calcd. for C7H7BrN2O, 215.0 (M+H), found 215.1.

Workup

  1. washthe mixture was washed with H2O (2×30 mL), brine (20 mL)
  2. dry with materialdried (Na2SO4)
  3. customThe organic solvent was evaporated in vacuo
  4. customthe residue was triturated with DCM

Sources & evidence

ORD record
ord-89f2685354a6411087e558d252c706db
Source dataset
uspto-grants-2010_09
Patent number
US07790724B2

Reaction notes

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