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

HRID 331047Notes

Reaction equation

HRID 331047 reaction equation
[Br:1][C:2]1[C:10]([F:11])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([N+:12]([O-])=O)[CH:3]=1.Cl.[Sn](Cl)[Cl:17]>O>[ClH:17].[NH2:12][C:4]1[CH:3]=[C:2]([Br:1])[C:10]([F:11])=[CH:9][C:5]=1[C:6]([OH:8])=[O:7]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24479Stannous ChlorideHCID 299192484-Bromo-5-fluoro-2-nitrobenzoic acid

Product 1

HCID 1272558832-Amino-4-bromo-5-fluorobenzoic acid hydrochlorideYield 83%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

To a mixture of 4-bromo-5-fluoro-2-nitrobenzoic acid (10 g, 37.9 mmol) and HCl (70 mL, 852 mmol) in water (70 mL) was added tin(II) chloride (21.55 g, 114 mmol) and the mixture was then heated at 90° C. for 3 hours. After cooling to RT, the formed precipitate was filtered, washed with water and collected to give title compound (8.51 g). LCMS (A): m/z [(M−HCl)+H]+ 234/236, C7H5BrFNO2.HCl requires 269/271 (acidic).

Workup

  1. temperatureAfter cooling to RT
  2. filtrationthe formed precipitate was filtered
  3. washwashed with water
  4. customcollected

Sources & evidence

ORD record
ord-05bc856972c04e4f88b6129307b3a6a3
Source dataset
uspto-grants-2014_11
Patent number
US08877742B2

Reaction notes

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