Iodine → Methyl 2-amino-5-fluoro-3-iodobenzoate

HRID 1987980Notes

Reaction equation

HRID 1987980 reaction equation
[I:1]I.[NH2:3][C:4]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7]>S([O-])([O-])(=O)=O.[Ag+2].C(O)C>[NH2:3][C:4]1[C:13]([I:1])=[CH:12][C:11]([F:14])=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7]

Participants

5

Reactant 2

HCID 807IodineHCID 2783401Methyl 2-amino-5-fluorobenzoate

Product 1

HCID 53621894Methyl 2-amino-5-fluoro-3-iodobenzoateYield 93.1%

Reagents, catalysts & solvents 2

HCID 178418844HCID 178418844, compoundCatalystHCID 702EthanolSolvent

Procedure

Iodine (3.6 g, 14.2 mmol) was added to a mixture of methyl 2-amino-5-fluorobenzoate (2.4 g, 14.2 mmol), silver sulfate (4.42 g, 14.2 mmol) and ethanol (30 mL) at room temperature. The mixture was stirred under nitrogen for 1 h, and then quenched with a saturated solution of sodium bicarbonate, extracted with ethyl acetate. The combined organic layers were washed with brine, dried (Na2SO4), filtered and concentrated. The crude material was purified by column chromatography (silica gel, 90:10 hexanes/ethyl acetate) to afford methyl 2-amino-5-fluoro-3-iodobenzoate (3.9 g, 93%) as a light yellow solid: 1H NMR (300 MHz, CDCl3) δ 7.66-7.58 (m, 2H), 6.21 (br s, 2H), 3.89 (s, 3H); 19F NMR (282 MHz, CDCl3) δ 127.87; MS (ESI+) m/z 296 (M+H).

Workup

  1. customquenched with a saturated solution of sodium bicarbonate
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude material was purified by column chromatography (silica gel, 90:10 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-dcc6d38242f54c2382400cecaad67051
Source dataset
uspto-grants-2009_06
Patent number
US07553846B2

Reaction notes

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