Hydrogen Bromide → N-[2-(2-bromoacetyl)phenyl]acetamide

HRID 1295429

Reaction equation

HRID 1295429 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][C:11](=[O:13])[CH3:12])(=[O:3])[CH3:2].[BrH:14].BrBr>C(O)(=O)C>[Br:14][CH2:2][C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][C:11](=[O:13])[CH3:12])=[O:3]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 21306N-(2-Acetylphenyl)acetamideHCID 24408Bromine

Product 1

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

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

31 g (0.175 mol) of N-(2-acetylphenyl)acetamide (prepared by acylating 2-aminoacetophenone with acetyl chloride according to Fuerstner, Alois; Jumbam, Denis N.; Tetrahedron; 48; 29; 5991-6010, (1992)) were dissolved in 200 ml of glacial acetic acid. 127 ml of 33% HBr in glacial acetic acid were added and then 8.75 ml (0.175 mol) of bromine were added slowly at room temperature. The mixture was stirred at room temperature overnight. The mixture was stirred into 1.5 l of ice-water, and the precipitated product was filtered off with suction, washed thoroughly with ice-water and dried in vacuo. According to HPLC and NMR, the crude product contained some reactant and dibrominated product, but was clean enough for the further reaction (approx. 85%).

Workup

  1. filtrationthe precipitated product was filtered off with suction
  2. washwashed thoroughly with ice-water
  3. customdried in vacuo
  4. customwas clean enough for the further reaction (approx. 85%)

Sources & evidence

ORD record
ord-18312d271e5c4a0681ef4da26ee8d9d8
Source dataset
uspto-grants-2007_07
Patent number
US07241775B2

Linked notes

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