N-bromobutanimide → 3-bromo-4-methoxyisobenzofuran-1(3H)-one

HRID 1091802Notes

Reaction equation

HRID 1091802 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH2:5][O:6][C:7]2=[O:12].[Br:13]N1C(=O)CCC1=O.N(/C(C)(C)C#N)=N\C(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:13][CH:5]1[C:4]2[C:8](=[CH:9][CH:10]=[CH:11][C:3]=2[O:2][CH3:1])[C:7](=[O:12])[O:6]1

Participants

5

Reactant 3

HCID 67184N-bromobutanimideHCID 111163794-METHOXYISOBENZOFURAN-1(3H)-ONEHCID 178449902HCID 178449902, compound

Product 1

HCID 109992163-bromo-4-methoxyisobenzofuran-1(3H)-oneYield 66.9%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
80 °C

Procedure

4-methoxyisobenzofuran-1(3H)-one (121) (3.18 g, 19.37 mmol) and 1-bromopyrrolidine-2,5-dione (3.62 g, 20.34 mmol) were dissolved in carbon tetrachloride (40 mL) and heated reflux. (E)-2,2′-(diazene-1,2-diyl)bis(2-methylpropanenitrile) (0.318 g, 1.94 mmol) was added and the reaction stirred overnight at 80° C. The reaction was allowed to cool and filtered. The solvent removed to afford the desired material as a orange solid (3.15 g, 66.9%), which was used without further purification; 1H NMR (400.132 MHz, DMSO) δ 3.91 (3H, s), 6.66 (1H, s), 7.35-7.40 (2H, m), 7.57-7.65 (1H, m).

Workup

  1. temperatureheated
  2. temperaturereflux
  3. temperatureto cool
  4. filtrationfiltered
  5. customThe solvent removed

Sources & evidence

ORD record
ord-c4a7fe6f8a6e47f6b650411286644e2f
Source dataset
uspto-grants-2012_03
Patent number
US08129380B2

Reaction notes

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