Naphthalic anhydride → 5-Bromobenzo[de]isochromene-1,3-dione

HRID 2105931Notes

Reaction equation

HRID 2105931 reaction equation
[Br:1]Br.[CH:3]1[CH:4]=[C:5]2[C:10]3=[C:11]([C:13]([O:15][C:16](=[O:17])[C:9]3=[CH:8][CH:7]=[CH:6]2)=[O:14])[CH:12]=1>[N+]([O-])(O)=O>[CH:3]1[CH:12]=[C:11]2[C:13]([O:15][C:16](=[O:17])[C:9]3=[C:10]2[C:5](=[CH:6][C:7]([Br:1])=[CH:8]3)[CH:4]=1)=[O:14]

Participants

4

Reactant 2

HCID 6693Naphthalic anhydrideHCID 24408Bromine

Product 1

HCID 39074915-Bromobenzo[de]isochromene-1,3-dioneYield 20%

Reagents, catalysts & solvents 1

HCID 944Nitric AcidSolvent

Conditions

Temperature
70 °C

Procedure

Bromine (13.2 mL, 256 mmol) was added to a stirred solution of 1,8-naphthalic anhydride (50 g, 252 mmol) in 70% nitric acid (1000 mL) at 25° C. over a period of 10 min. The resulting brown solution was stirred at 70° C. for 2 hrs and cooled overnight. The cream colored precipitate was collected by filtration and washed with water (4×150 mL). The isolated product was dried in vacuum for 24 hrs, resulting in off-white crystalline solid (12.0 g, 20% yield).

Workup

  1. temperaturecooled overnight
  2. filtrationThe cream colored precipitate was collected by filtration
  3. washwashed with water (4×150 mL)
  4. customThe isolated product was dried in vacuum for 24 hrs

Sources & evidence

ORD record
ord-a6657b33d2a24f4cbf1c9fc6ba074cde
Source dataset
uspto-grants-2009_08
Patent number
US07579468B2

Reaction notes

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