5-Chlorosalicylic Acid → HCID 59204940, compound

HRID 2241917Notes

Reaction equation

HRID 2241917 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[F:9].P(Cl)(Cl)Cl.[Cl:14][C:15]1[CH:23]=[C:19]([C:20](O)=[O:21])[C:18]([OH:24])=[CH:17][CH:16]=1.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:20](=[O:21])[C:19]2[CH:23]=[C:15]([Cl:14])[CH:16]=[CH:17][C:18]=2[OH:24])=[CH:4][C:3]=1[F:9]

Participants

6

Reactant 4

HCID 94475-Chlorosalicylic AcidHCID 24387Phosphorus trichlorideHCID 516892Sodium BicarbonateHCID 8218484-Bromo-3-fluoroaniline

Product 1

HCID 59204940HCID 59204940, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4-Bromo-3-fluoroaniline (0.570 g, 3.00 mmol) and phosphorus trichloride (0.176 ml, 2.0 mmol) were added to a solution of 5-chlorosalicylic acid (0.690 g, 4.00 mmol) in toluene (30 ml), and the mixture was refluxed for 2 hours. Saturated aqueous sodium hydrogencarbonate was added to the reaction mixture, and the mixture was concentrated under reduced pressure and extracted with tetrahydrofuran. The organic layer was washed with saturated aqueous sodium hydrogencarbonate and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the title compound (0.930 g, 90%) as a white solid.

Workup

  1. temperaturethe mixture was refluxed for 2 hours
  2. concentrationthe mixture was concentrated under reduced pressure
  3. extractionextracted with tetrahydrofuran
  4. washThe organic layer was washed with saturated aqueous sodium hydrogencarbonate
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-65265368cd2644c083bad89481fadae0
Source dataset
uspto-grants-2010_03
Patent number
US07671058B2

Reaction notes

Loading…