Hydrochloric Acid → 2-Amino-4-bromo-5-fluorobenzoic acid

HRID 517448Notes

Reaction equation

HRID 517448 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6](=[O:12])C(=O)[NH:8]2)=[CH:4][C:3]=1[F:13].[OH-:14].[Na+].OO.Cl>>[NH2:8][C:9]1[CH:10]=[C:2]([Br:1])[C:3]([F:13])=[CH:4][C:5]=1[C:6]([OH:12])=[O:14]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 675170396-Bromo-5-fluoroindoline-2,3-dione

Product 1

HCID 675149612-Amino-4-bromo-5-fluorobenzoic acidYield 25%

Conditions

Temperature
0 °C

Procedure

To a 100 mL round bottom flask, 6-bromo-5-fluoro-1H-indole-2,3-dione (3 g, 0.0121 mol) and 2N NaOH (15 mL) were added and cooled the reaction vessel to 0° C. To this reaction mixture 30% hydrogen peroxide (10.5 mL) was slowly added. The reaction mixture was stirred at 0° C. for 3 h. Subsequently, the reaction mixture was acidified with 2 N HCl at 0° C. [pH-5] to afford the solid compound. The solid material was collected by filtration and dried to obtain the title compound (700 mg, 25%). 1H NMR (300 MHz, DMSO-d6): δ 7.52 (d, J=9.6 Hz, 1H), 7.09 (d, J=6.0 Hz, 1H); LC-MS (ESI): Calculated mass: 232.9; Observed mass: 231.9 [M−H]+ (RT: 0.23 min).

Workup

  1. customto afford the solid compound
  2. filtrationThe solid material was collected by filtration
  3. customdried

Sources & evidence

ORD record
ord-a5da36e5b3ec4c68bfb546032b1a9df2
Source dataset
uspto-grants-2015_08
Patent number
US09115092B2

Reaction notes

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