Hydrochloric Acid → 5-Bromoisatoic Anhydride

HRID 989674Notes

Reaction equation

HRID 989674 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH2:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].C1C[O:15][CH2:14]C1.Cl.C(Cl)(Cl)=O>O>[Br:1][C:2]1[CH:10]=[C:6]2[C:7]([O:9][C:14](=[O:15])[NH:11][C:5]2=[CH:4][CH:3]=1)=[O:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6371PhosgeneHCID 8028TetrahydrofuranHCID 798582-Amino-5-bromobenzoic acid

Product 1

HCID 2885615-Bromoisatoic AnhydrideYield 78%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of 5-bromo-2-amino-benzoic acid (25 g, 0.115 mmol) in a mixed solvent of THF:H2O:conc. HCl (4:2:1, 350 mL), was added a solution of phosgene (0.23 mmol, 20% in toluene) dropwise. The reaction mixture was allowed to stir at room temperature for 4 h. The resulting precipitate was filtered, washed with water and dried under reduced pressure to give the title compound (22.5 g, 78%) as a gray solid.

Workup

  1. filtrationThe resulting precipitate was filtered
  2. washwashed with water
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-96eff181ceb84137ba8bcb280d41e14b
Source dataset
uspto-grants-2002_10
Patent number
US06458783B1

Reaction notes

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