Isatoic Anhydride → 5-Bromoisatoic Anhydride

HRID 2079289Notes

Reaction equation

HRID 2079289 reaction equation
[Br:1]Br.[C:3]12[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=1)[NH:8][C:7](=[O:14])[O:6][C:4]2=[O:5]>O>[Br:1][C:12]1[CH:11]=[CH:10][C:9]2[NH:8][C:7](=[O:14])[O:6][C:4](=[O:5])[C:3]=2[CH:13]=1

Participants

4

Reactant 2

HCID 8359Isatoic AnhydrideHCID 24408Bromine

Product 1

HCID 2885615-Bromoisatoic AnhydrideYield 85.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Bromine (35 mL, 660 mmol) was added dropwise to a suspension of isatoic anhydride (100 g, 610 mmol) in 1.6 L water at 50° C. This temperature was maintained for an additional 2 hours. After cooling the solution to room temperature, the solid was filtered and washed twice with water and twice with acetone, yielding 125.6 g (85%) 6-bromo-1H-benzo[d][1,3]oxazine-2,4-dione as a pink solid.

Workup

  1. temperatureThis temperature was maintained for an additional 2 hours
  2. filtrationthe solid was filtered
  3. washwashed twice with water and twice with acetone

Sources & evidence

ORD record
ord-0d1d7bbf4d9a4d268251ff6820b0155c
Source dataset
uspto-grants-2011_04
Patent number
US07928107B2

Reaction notes

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