Iodine → Methyl 2-amino-4-chloro-5-iodobenzoate

HRID 2174540Notes

Reaction equation

HRID 2174540 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[I:13]I>C(O)C.S([O-])([O-])(=O)=O.[Ag+2]>[NH2:1][C:2]1[CH:11]=[C:10]([Cl:12])[C:9]([I:13])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

5

Reactant 2

HCID 807IodineHCID 80001Methyl 4-chloroanthranilate

Product 1

HCID 10852539Methyl 2-amino-4-chloro-5-iodobenzoateYield 55.7%

Reagents, catalysts & solvents 2

HCID 178418844HCID 178418844, compoundCatalystHCID 702EthanolSolvent2×

Procedure

To a solution of methyl 2-amino-4-chlorobenzoate (Aldrich, 111 g, 600 mmol) and silver sulfate (187 g, 600 mmol) in ethanol (1000 mL) was added dropwise in 8 hours a solution of iodine (152 g, 600 mmol) in ethanol (2000 mL). The reaction mixture was stirred overnight then filtered through a celite plug. The filtrate was concentrated under reduced pressure and the residue was triturated in n-heptane. The resulting solid was filtered, washed with diisopropyl ether to give the title compound methyl 2-amino-4-chloro-5-iodobenzoate (103.76 g, 334 mmol, 55.6% yield) as a white powder. LCMS: (M+H)+=312; Rt=3.46 min.

Workup

  1. filtrationthen filtered through a celite plug
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customthe residue was triturated in n-heptane
  4. filtrationThe resulting solid was filtered
  5. washwashed with diisopropyl ether

Sources & evidence

ORD record
ord-ecd28a29e865474eb7bdc480d484d83b
Source dataset
uspto-grants-2015_06
Patent number
US09061998B2

Reaction notes

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