Bis(pyridine)iodonium tetrafluoroborate → Ethyl 2-(4-amino-2-chloro-5-iodophenoxy)-4-fluorobenzoate

HRID 1043115Notes

Reaction equation

HRID 1043115 reaction equation
[NH2:1][C:2]1[CH:20]=[CH:19][C:5]([O:6][C:7]2[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:8]=2[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:4]([Cl:21])[CH:3]=1.[B-](F)(F)(F)F.C1C=CN=CC=1.C1C=CN=CC=1.[IH2+:39]>ClCCl.C(OCC)(=O)C>[NH2:1][C:2]1[C:20]([I:39])=[CH:19][C:5]([O:6][C:7]2[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:8]=2[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:4]([Cl:21])[CH:3]=1

Participants

5

Reactant 2

HCID 10883201Bis(pyridine)iodonium tetrafluoroborateHCID 67228057Ethyl 2-(4-amino-2-chlorophenoxy)-4-fluorobenzoate

Product 1

HCID 67228200Ethyl 2-(4-amino-2-chloro-5-iodophenoxy)-4-fluorobenzoate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of EXAMPLE 242A (8.15 g) in dichloromethane (60 mL) was added bis(pyridine)iodonium tetrafluoroborate (9.79 g). The mixture was stirred at room temperature for 4 hours. The mixture was diluted with ethyl acetate (200 mL) and washed with aqueous Na2S2O3, 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 pure product.

Workup

  1. washwashed with aqueous Na2S2O3, 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 pure product

Sources & evidence

ORD record
ord-6071ee8c792d46f9a3256daac59c6b39
Source dataset
uspto-grants-2013_10
Patent number
US08557983B2

Reaction notes

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