Hydrogen Bromide → HCID 57514834, compound

HRID 1984751Notes

Reaction equation

HRID 1984751 reaction equation
N[C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9](=[O:11])[CH3:10].[BrH:12].N([O-])=O.[Na+]>O.[Cu]Br>[Br:12][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9](=[O:11])[CH3:10]

Participants

6

Reactant 3

HCID 260Hydrogen Bromide2×HCID 1796281-(2-Amino-3-methylphenyl)ethan-1-oneHCID 23668193Sodium Nitrite

Product 1

HCID 57514834HCID 57514834, compoundYield 87.3%

Reagents, catalysts & solvents 2

HCID 24593copper(I) bromideCatalystHCID 962WaterSolvent

Conditions

Temperature
95 °C

Procedure

To a solution of 1-(2-amino-3-methylphenyl)ethanone (Helv. Chim. Acta; EN; 62, 1979, 271-303) (850 mg, 5.7 mmol) in hydrobromic acid (9 ml, 5.7 mmol) and water (6 ml), at 0° C., was added aqueous sodium nitrite solution (503 mg, 7.3 mmol) and the mixture was stirred for 15 min. This mixture was added to copper (I) bromide (899 mg, 6.3 mmol) in hydrobromic acid (9 ml, 5.7 mmol) at 60° C. and the reaction mixture was heated at 95° C. for a further 30 min. After cooling, the mixture was poured into an ice/water slurry and extracted with ethyl acetate. The combined extracts were dried (MgSO4) and concentrated in vacuo. To the residue was added ethyl acetate:cyclohexane [1:4] and the solution was filtered through silica. The filtrate was concentrated in vacuo to give the title compound (1.06 g).

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined extracts were dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. additionTo the residue was added ethyl acetate
  6. filtrationcyclohexane [1:4] and the solution was filtered through silica
  7. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-30f00095ac0b43cc9d9f008dbb336080
Source dataset
uspto-grants-2009_06
Patent number
US07544706B2

Reaction notes

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