Sulfuric Acid → 6-Bromo-5-fluoroindoline-2,3-dione

HRID 517447Notes

Reaction equation

HRID 517447 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:9][C:10](=[O:14])[CH:11]=NO)[CH:5]=[CH:6][C:7]=1[F:8].S(=O)(=O)(O)[OH:16]>>[Br:1][C:2]1[CH:3]=[C:4]2[C:5]([C:11](=[O:16])[C:10](=[O:14])[NH:9]2)=[CH:6][C:7]=1[F:8]

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 86665761N-(3-bromo-4-fluoro-phenyl)-2-hydroxyimino-acetamide

Product 1

HCID 675170396-Bromo-5-fluoroindoline-2,3-dioneYield 80%

Conditions

Temperature
90 °C

Procedure

To the concentrated sulfuric acid (40 mL) at 50° C. was added N-(3-bromo-4-fluoro-phenyl)-2-hydroxyimino-acetamide (4 g, 0.0152 mol). The temperature was raised to 90° C. and maintained for 3 h. The reaction mixture was added to ice cold water to get the precipitate. The precipitate was filtered and dried to get the title compound (3.0 g, 80%). LC-MS (ESI): Calculated mass: 243.0; Observed mass: 242.1 [M−H]+ (RT: 0.47 min).

Workup

  1. temperaturemaintained for 3 h
  2. additionThe reaction mixture was added to ice cold water
  3. customto get the precipitate
  4. filtrationThe precipitate was filtered
  5. customdried

Sources & evidence

ORD record
ord-88cd70df74df46c2b0819221932bc236
Source dataset
uspto-grants-2015_08
Patent number
US09115092B2

Reaction notes

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