N-(2-Acetylphenyl)acetamide → N-[2-(2-bromoacetyl)phenyl]acetamide

HRID 1782709

Reaction equation

HRID 1782709 reaction equation
[Br:1]Br.[C:3]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13](=[O:15])[CH3:14])(=[O:5])[CH3:4]>C(Cl)(Cl)Cl>[C:3]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13](=[O:15])[CH2:14][Br:1])(=[O:5])[CH3:4]

Participants

4

Reactant 2

HCID 21306N-(2-Acetylphenyl)acetamideHCID 24408Bromine

Product 1

HCID 2749459N-[2-(2-bromoacetyl)phenyl]acetamide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

45.0 g (0.282 mol) of dry bromine were added dropwise to a boiling solution of 50.0 g (0.282 mol) of 1-[2-(acetylamino)phenyl]ethanone in 400 ml of chloroform at room temperature. The solvent was distilled off, the residue was distributed between dichloromethane and saturated ice-cold sodium hydrogen carbonate solution. The organic phase was dried over sodium sulphate, evaporated down in vacuo, the residue was triturated with diethylether and suction filtered. After drying in vacuo 35.4 g (49% of theory) of colourless crystals were obtained, Rf=0.48 (eluant: petroleum ether/ethyl acetate 2/1 v/v).

Workup

  1. distillationThe solvent was distilled off
  2. dry with materialThe organic phase was dried over sodium sulphate
  3. customevaporated down in vacuo
  4. customthe residue was triturated with diethylether and suction
  5. filtrationfiltered
  6. customAfter drying in vacuo 35.4 g (49% of theory) of colourless crystals
  7. customwere obtained

Sources & evidence

ORD record
ord-926f7b0a23cc4338b77caa0fd2afa495
Source dataset
uspto-grants-2009_03
Patent number
US07498325B2

Linked notes

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