m-Nitroacetophenone → 2-Bromo-1-(3-nitrophenyl)ethan-1-one

HRID 221399

Reaction equation

HRID 221399 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10](=[O:12])[CH3:11])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[Br-:13].[Br-].[Br-].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>C(O)(=O)C>[Br:13][CH2:11][C:10]([C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)=[O:12]

Participants

4

Reactant 2

HCID 8494m-NitroacetophenoneHCID 21124087Pyridiniumtribromide

Product 1

HCID 752132-Bromo-1-(3-nitrophenyl)ethan-1-oneYield 127.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

m-Nitroacetophenone (20 g) was dissolved in acetic acid (150 mL) under argon. Pyridinium tribromide (38.7 g) was added at once; the reaction was allowed to stir at room temperature for 1 hour and then quenched with water (250 mL). The product was filtered and air dried to give the title compound (25 g, 84%).

Workup

  1. customquenched with water (250 mL)
  2. filtrationThe product was filtered
  3. customair dried

Sources & evidence

ORD record
ord-c14ea3eb512c47819ba451df036c0cd2
Source dataset
uspto-grants-2012_06
Patent number
US08207167B2

Linked notes

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