Ethyl Acetate → 4-Cyano-2,6-difluorobenzoic acid

HRID 1772795Notes

Reaction equation

HRID 1772795 reaction equation
P([O-])([O-])([O-])=O.[K+].[K+].[K+].[F:9][C:10]1[CH:11]=[C:12]([CH:15]=[C:16]([F:20])[C:17]=1[CH:18]=[O:19])[C:13]#[N:14].Cl([O-])=[O:22].[Na+].C(OCC)(=O)C>O.CS(C)=O>[C:13]([C:12]1[CH:11]=[C:10]([F:9])[C:17]([C:18]([OH:22])=[O:19])=[C:16]([F:20])[CH:15]=1)#[N:14]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 62657Potassium Phosphate, TribasicHCID 162182563,5-Difluoro-4-formylbenzonitrileHCID 23668197Sodium Chlorite

Product 1

HCID 445579334-Cyano-2,6-difluorobenzoic acid

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent3×

Procedure

Potassium phosphate, monobasic (1.0 g, 7.5 mmol) in water (10 mL) was added to a solution of 3,5-difluoro-4-formylbenzonitrile (0.50 g, 0.0030 mol, Aldrich) in DMSO (10 mL). Sodium chlorite (0.7 g, 0.006 mol) in water (10 mL) was added and the reaction was stirred for 1 hour. Ethyl acetate and water were added. Layers were separated, and the aqueous was saturated with solid NaCl and extracted with further ethyl acetate. The combined organic extracts were washed with sat. NaCl, dried and rotovapped to give a white solid. 1H NMR (300 MHz, d6-dmso): δ 7.98-7.91 (m, 2H).

Workup

  1. customLayers were separated
  2. extractionextracted with further ethyl acetate
  3. washThe combined organic extracts were washed with sat. NaCl
  4. customdried
  5. customto give a white solid

Sources & evidence

ORD record
ord-75f8a506235d4367ac21c36dbcc6138d
Source dataset
uspto-grants-2016_02
Patent number
US09249145B2

Reaction notes

Loading…