Lithium iodide → 3-Cyano-5-(trifluoromethyl)benzoic acid

HRID 1640147Notes

Reaction equation

HRID 1640147 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:12]=1)[C:6]([O:8]C)=[O:7])#[N:2].[I-].[Li+]>N1C=CC=CC=1>[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([C:13]([F:14])([F:15])[F:16])[CH:12]=1)[C:6]([OH:8])=[O:7])#[N:2]

Participants

4

Reactant 2

HCID 66321Lithium iodideHCID 58902345Methyl 3-cyano-5-(trifluoromethyl)benzoate

Product 1

HCID 589022873-Cyano-5-(trifluoromethyl)benzoic acidYield 92.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of methyl 3-cyano-5-(trifluoromethyl)benzoate (2.67 g, 0.0105 mol) and lithium iodide (13 g, 0.070 mol) in pyridine (70 mL) was subjected to MWI for 30 min at 100° C. The mixture was concentrated and residue was extracted with EtOAc. The organic solutions were combined, washed with 1N HCl(, water and brine, dried over Na2SO4, filtered, and concentrated. The residue was redissolved in EtOAc, washed by 0.2N HCl and brine, dried and concentrated to give 3-cyano-5-(trifluoromethyl)benzoic acid (2.09 g. 92%). 1H NMR (400 MHz, d6-DMSO) δ: 8.58 (s, 1H), 8.55 (s, 1H), and 8.39 (s, 1H). LCMS: ES− 214.2.

Workup

  1. concentrationThe mixture was concentrated
  2. extractionresidue was extracted with EtOAc
  3. washwashed with 1N HCl(, water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. dissolutionThe residue was redissolved in EtOAc
  8. washwashed by 0.2N HCl and brine
  9. customdried
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-2d493aab6646432396e7457d3e105927
Source dataset
uspto-grants-2012_02
Patent number
US08110687B2

Reaction notes

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