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

HRID 624382

Reaction equation

HRID 624382 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 Na_SO4. 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 Na_SO4
  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-e5eaae9f9c504cbd97cb794476cb4a6c
Source dataset
uspto-grants-2016_04
Patent number
US09303025B2

Linked notes

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