N-Iodosuccinimide → Methyl 2-amino-3-iodo-5-(trifluoromethyl)benzoate

HRID 2203150Notes

Reaction equation

HRID 2203150 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[I:16]N1C(=O)CCC1=O>FC(F)(F)C(O)=O>[NH2:1][C:2]1[C:11]([I:16])=[CH:10][C:9]([C:12]([F:13])([F:14])[F:15])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 14233808Methyl 2-amino-5-(trifluoromethyl)benzoate

Product 1

HCID 118251642Methyl 2-amino-3-iodo-5-(trifluoromethyl)benzoateYield 68%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of methyl 2-amino-5-(trifluoromethyl)benzoate (0.59 g, 2.7 mmoles) in trifluoroacetic acid (5 ml) was treated with N-iodosuccinimide (0.68 g, 3.0 mmoles) and stirred at ambient temperature for 18 h. The mixture was evaporated to dryness and the residue treated with water (25 ml) and basified with potassium carbonate then extracted with dichloromethane (25 ml). The organic phase was then washed with 10% sodium metabisulphite solution (25 ml), separated and dried over sodium sulphate, filtered and evaporated to dryness. The residue was chromatographed on silica gel eluting with an ethyl acetate/isohexane gradient. This gave the title compound 2 as a white solid (0.633 g, 68%).

Workup

  1. customThe mixture was evaporated to dryness
  2. additionthe residue treated with water (25 ml)
  3. extractionthen extracted with dichloromethane (25 ml)
  4. washThe organic phase was then washed with 10% sodium metabisulphite solution (25 ml)
  5. customseparated
  6. dry with materialdried over sodium sulphate
  7. filtrationfiltered
  8. customevaporated to dryness
  9. customThe residue was chromatographed on silica gel eluting with an ethyl acetate/isohexane gradient

Sources & evidence

ORD record
ord-f2d3700a8c664e86aa01a491d7fac35b
Source dataset
uspto-grants-2016_06
Patent number
US09365569B2

Reaction notes

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