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

HRID 566967

Reaction equation

HRID 566967 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 14.3%

Reagents, catalysts & solvents 1

HCID 944Nitric AcidSolvent

Conditions

Temperature
70 °C

Procedure

Bromine (8.2 g, 51.3 mmol) was added to a solution of 1,8-naphthalic anhydride (10.0 g, 50.5 mmol) in 70% nitric acid (200 mL) at 25° C. The mixture was stirred at 70° C. for 2 hours and cooled overnight. The solids that separated were filtered, washed with water, and dried to give 2.0 g of the title compound (Reference: J. C. S., 1938:1764-1767).

Workup

  1. temperaturecooled overnight
  2. customThe solids that separated
  3. filtrationwere filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-db34d90323284cb1be3c803611f4da48
Source dataset
uspto-grants-2001_01
Patent number
US06177423B1

Linked notes

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