Phosgene → 4-Bromoisatoic anhydride

HRID 1270404Notes

Reaction equation

HRID 1270404 reaction equation
[C:1](Cl)(Cl)=[O:2].[NH2:5][C:6]1[CH:14]=[C:13]([Br:15])[CH:12]=[CH:11][C:7]=1[C:8]([OH:10])=[O:9]>C1COCC1.Cl>[Br:15][C:13]1[CH:12]=[CH:11][C:7]2[C:8](=[O:10])[O:9][C:1](=[O:2])[NH:5][C:6]=2[CH:14]=1

Participants

5

Reactant 2

HCID 6371PhosgeneHCID 886912-Amino-4-bromobenzoic acid

Product 1

HCID 115215774-Bromoisatoic anhydride

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

Phosgene (1.9 M in toluene, 18.4 mL, 35 mmol) was added dropwise over 1 h to a solution of 2-amino-4-bromobenzoic acid from Step A (2.5 g, 11.7 mmol) in THF (30 mL) and 1 N HCl (20 mL). After 2 h, the precipitate was collected by filtration, washed with H2O, then ethyl acetate, and dried in vacuo to give the title compound. MS: m/z=242 (M+1).

Workup

  1. filtrationthe precipitate was collected by filtration
  2. washwashed with H2O
  3. dry with materialethyl acetate, and dried in vacuo

Sources & evidence

ORD record
ord-9d6ecf80ddb141a3a5903888b2c92c04
Source dataset
uspto-grants-2007_04
Patent number
US07202251B2

Reaction notes

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