Iodine → Methyl 2-amino-5-iodo-4-(trifluoromethyl)benzoate

HRID 906501Notes

Reaction equation

HRID 906501 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])[F:11])=[CH:6][C:5]=1[NH2:14].[I:16]I>CCO.S([O-])([O-])(=O)=O.[Ag+2]>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8]([I:16])[C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:5]=1[NH2:14]

Participants

5

Reactant 2

HCID 807IodineHCID 12601886Methyl 2-Amino-4-(trifluoromethyl)benzoate

Product 1

HCID 53436880Methyl 2-amino-5-iodo-4-(trifluoromethyl)benzoateYield 90.3%

Reagents, catalysts & solvents 2

HCID 178418844HCID 178418844, compoundCatalystHCID 702EthanolSolvent

Procedure

A mixture of 2-amino-4-trifluoromethyl-benzoic acid methyl ester (51.5 g, 235 mmol), iodine (55.1 g, 217 mmol) and silver sulfate (73.3 g, 234 mmol) in EtOH (1560 mL) was stirred for 1 h at r.t. under nitrogen. The suspension was then filtered and the filtrate diluted with EtOAc and washed once with a 10% aqueous sodium thiosulfate solution. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give 2-amino-5-iodo-4-trifluoromethyl-benzoic acid methyl ester (67.5 g, 196 mmol, 83%) as a brown solid, m.p. 101-103° C., ESI-MS: m/z 346 [M+H]+.

Workup

  1. filtrationThe suspension was then filtered
  2. additionthe filtrate diluted with EtOAc
  3. washwashed once with a 10% aqueous sodium thiosulfate solution
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b55f293de0314813ae59fbf1ac609411
Source dataset
uspto-grants-2011_09
Patent number
US08012988B2

Reaction notes

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