Potassium Phosphate, Tribasic → Ethyl 2-(4-amino-2-chlorophenoxy)-4-fluorobenzoate

HRID 624381Notes

Reaction equation

HRID 624381 reaction equation
F[C:2]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].[NH2:14][C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[C:17]([Cl:22])[CH:16]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>COCCOCCOC.C(OCC)(=O)C>[NH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][C:2]2[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:3]=2[C:4]([O:6][CH2:7][CH3:8])=[O:5])=[C:17]([Cl:22])[CH:16]=1

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 775784-Amino-2-chlorophenolHCID 2737170Benzoic acid, 2,4-difluoro-, ethyl ester

Product 1

HCID 67228057Ethyl 2-(4-amino-2-chlorophenoxy)-4-fluorobenzoate

Reagents, catalysts & solvents 2

HCID 8150DiglymeSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of ethyl 2,4-difluorobenzoate (6.48 g) and 4-amino-2-chlorophenol (5.0 g) in diglyme (40 mL) was added K3PO4 (7.39 g). The mixture was stirred at 110° C. overnight. The mixture was diluted with ethyl acetate (300 mL) and washed with water, brine and dried over Na2SO4. The mixture was filtered, and the solvent was evaporated and the residue was loaded on a column and eluted with 10% ethyl acetate in hexane to give the product.

Workup

  1. washwashed with water, brine
  2. dry with materialdried over Na2SO4
  3. filtrationThe mixture was filtered
  4. customthe solvent was evaporated
  5. washeluted with 10% ethyl acetate in hexane
  6. customto give the product

Sources & evidence

ORD record
ord-f15eb27099864222b7908112ddccfe35
Source dataset
uspto-grants-2016_04
Patent number
US09303025B2

Reaction notes

Loading…