N-Iodosuccinimide → Methyl 2-amino-5-fluoro-3-iodobenzoate

HRID 1919680Notes

Reaction equation

HRID 1919680 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[I:13]N1C(=O)CCC1=O>C(O)(=O)C>[NH2:1][C:2]1[C:11]([I:13])=[CH:10][C:9]([F:12])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 2783401Methyl 2-amino-5-fluorobenzoate

Product 1

HCID 53621894Methyl 2-amino-5-fluoro-3-iodobenzoate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Methyl 2-amino-5-fluorobenzoate (1.0 eq, 8.47 g, 0.051 mol) was reacted with N-Iodo succinimide (1.03 eq, 11.6 g, 0.0515 mol) in acetic acid (100 ml) at room temperature for 20 minutes. The solvent was removed in vacuo. A K2CO3 aqueous solution was added and the compound extracted with ethylacetate. The organic layer was washed with 1M sodium thiosulfate, water and then brine. After drying over Na2SO4, and evaporation of the solvent, methyl 2-amino-5-fluoro-3-iodobenzoate was isolated as a purple solid (14.21 g, 96% yield). 1H NMR (CDCl3, 400 MHz) δ 3.8 (s, 3H), 6.3 (br s, 2H), 7.6 (m, 2H) ppm.

Workup

  1. customThe solvent was removed in vacuo
  2. additionA K2CO3 aqueous solution was added
  3. extractionthe compound extracted with ethylacetate
  4. washThe organic layer was washed with 1M sodium thiosulfate, water
  5. dry with materialAfter drying over Na2SO4, and evaporation of the solvent

Sources & evidence

ORD record
ord-2d7bfca36d2442a4a42462f1cb02d6bc
Source dataset
uspto-grants-2012_05
Patent number
US08168651B2

Reaction notes

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