Methanol → HCID 86653321, compound

HRID 2093787Notes

Reaction equation

HRID 2093787 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([CH3:11])=[CH:4][C:3]=1[C:12](=[O:14])[CH3:13].CO.[Br:17]Br>Br.O>[Br:17][CH2:13][C:12]([C:3]1[CH:4]=[C:5]([CH3:11])[C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=1[CH3:1])=[O:14]

Participants

6

Reactant 3

HCID 887MethanolHCID 24408BromineHCID 67167386HCID 67167386, compound

Product 1

HCID 86653321HCID 86653321, compound

Reagents, catalysts & solvents 2

HCID 260Hydrogen BromideSolventHCID 962WaterSolvent

Procedure

To a mixture of 1-(2,5-dimethyl-4-nitrophenyl)ethanone (300 mg, 1.55 mmol) in HBr (48%) (5 mL)/methanol (2.4 mL) was added bromine (250 mg, 1.55 mmol). The mixture was stirred at room temperature for 4 hrs. The mixture was diluted with water and extracted with ethyl acetate (2×20 mL). The organic layer was washed with brine and concentrated. The residue was purified with silica gel column chromatography (10% ethyl acetate in hexanes) to afford 2-bromo-1-(2,5-dimethyl-4-nitrophenyl)ethanone as a white solid.

Workup

  1. extractionextracted with ethyl acetate (2×20 mL)
  2. washThe organic layer was washed with brine
  3. concentrationconcentrated
  4. customThe residue was purified with silica gel column chromatography (10% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-63005fe0d1f3422b929d599a1248ab80
Source dataset
uspto-grants-2013_05
Patent number
US08445505B2

Reaction notes

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