N-bromobutanimide → HCID 57517516, compound

HRID 2368155Notes

Reaction equation

HRID 2368155 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([N+:13]([O-:15])=[O:14])[CH:7]=2)[CH2:3][CH2:2]1.[Br:16]N1C(=O)CCC1=O>C(OCC)(=O)C.N(C(C)(C)C#N)=NC(C)(C)C#N>[Br:16][CH2:12][C:9]1[CH:10]=[CH:11][C:6]([O:5][CH2:4][CH:1]2[CH2:3][CH2:2]2)=[CH:7][C:8]=1[N+:13]([O-:15])=[O:14]

Participants

5

Reactant 2

HCID 67184N-bromobutanimide2×HCID 57517515HCID 57517515, compound

Product 1

HCID 57517516HCID 57517516, compoundYield 54.4%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalyst2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

To a mixture of 4-(cyclopropylmethoxy)-1-methyl-2-nitrobenzene (66.4 g) and a solution of N-bromosuccinimide (68.4 g) in ethyl acetate (1.0 L) was added 2,2′-azobis(2-methylpropionitrile) (2.63 g) in 5 portions at 90° C. The reaction mixture was stirred at 90° C. overnight. To the reaction mixture were added N-bromosuccinimide (34.2 g) and 2,2′-azobis(2-methylpropionitrile) (1.32 g) at 90° C. The mixture was allowed to cool to room temperature, concentrated under reduced pressure and left standing overnight. The resulting crystals were collected by filtration, washed with methanol, and dried under reduced pressure to give the title compound (49.9 g).

Workup

  1. temperatureto cool to room temperature
  2. concentrationconcentrated under reduced pressure
  3. waitleft
  4. waitstanding overnight
  5. filtrationThe resulting crystals were collected by filtration
  6. washwashed with methanol
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-c43e1b5ebd4b4c01836ce71927d19cab
Source dataset
uspto-grants-2014_04
Patent number
US08703758B2

Reaction notes

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