Iodine → Methyl 2-amino-4-(1,1-difluoroethyl)-5-iodobenzoate

HRID 906606Notes

Reaction equation

HRID 906606 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[CH3:11])=[CH:6][C:5]=1[NH2:14].[I:16]I>CCO.[O-]S([O-])(=O)=O.[Ag+].[Ag+]>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8]([I:16])[C:7]([C:10]([F:12])([F:13])[CH3:11])=[CH:6][C:5]=1[NH2:14]

Participants

5

Reactant 2

HCID 807IodineHCID 59164446Methyl 2-amino-4-(1,1-difluoroethyl)benzoate

Product 1

HCID 59164486Methyl 2-amino-4-(1,1-difluoroethyl)-5-iodobenzoateYield 96.2%

Reagents, catalysts & solvents 2

HCID 159865Silver sulfateCatalystHCID 702EthanolSolvent

Procedure

A mixture of 2-amino-4-(1,1-difluoro-ethyl)-benzoic acid methyl ester (1.3 g, 6.04 mmol), I2 (1.53 g, 6.03 mmol) and Ag2SO4 (1.89 g, 6.03 mmol) in EtOH (40 mL) was stirred for 1 h at r.t. The suspension was then filtered and the filtrate diluted with EtOAc and washed once with a 10% aqueous Na2SO3. The organic layer was dried (Na2SO4), filtered and concentrated in vacuo to give 2-amino-4-(1,1-difluoro-ethyl)-5-iodo-benzoic acid methyl ester (1.98 g, 5.8 mmol, 96%) as a brown solid, ESI-MS: m/z 383 [M+CH3CN+H]+. rt 6.71 min

Workup

  1. filtrationThe suspension was then filtered
  2. additionthe filtrate diluted with EtOAc
  3. washwashed once with a 10% aqueous Na2SO3
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4e4dadeea26242a9a7c8568e32d3ed17
Source dataset
uspto-grants-2011_09
Patent number
US08012988B2

Reaction notes

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