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

HRID 46221

Reaction equation

HRID 46221 reaction equation
[CH:1]1[CH:2]=[C:3]2[C:8]3=[C:9]([C:11]([O:13][C:14](=[O:15])[C:7]3=[CH:6][CH:5]=[CH:4]2)=[O:12])[CH:10]=1.[Br:16]Br>>[CH:1]1[CH:10]=[C:9]2[C:11]([O:13][C:14](=[O:15])[C:7]3=[C:8]2[C:3](=[CH:4][C:5]([Br:16])=[CH:6]3)[CH:2]=1)=[O:12]

Participants

3

Reactant 2

HCID 6693Naphthalic anhydride2×HCID 24408Bromine

Product 1

HCID 39074915-Bromobenzo[de]isochromene-1,3-dioneYield 22.7%

Conditions

Temperature
50 °C

Procedure

1,8-Naphthalic anhydride (compound 73, 100 g, 505 mmol) was slurried in c-nitric acid (70%, 2.0 L) and heated to 50° C. Bromine (19.4 mL, 379 mmol) was added evenly over 10 min, and the resulting solution was held at 50° C. for 4 h before cooling to 0° C. The resulting solid was isolated by filtration and dried in vacuo to yield the title compound (23.8 g, 17%) as a white solid.

Workup

  1. temperaturebefore cooling to 0° C
  2. customThe resulting solid was isolated by filtration
  3. customdried in vacuo

Sources & evidence

ORD record
ord-afe565aab61141c8be7f5c055846b6df
Source dataset
uspto-grants-2013_09
Patent number
US08541380B2

Linked notes

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