Iodine → HCID 71236679, compound

HRID 920306Notes

Reaction equation

HRID 920306 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[C:11]([F:16])[CH:10]=2)=[N:6][CH:7]=1.C([Mg]Cl)(C)C.[I:22]I.[NH4+].[Cl-]>O1CCCC1.CCOC(C)=O>[F:16][C:11]1[CH:10]=[C:9]([CH:14]=[CH:13][C:12]=1[F:15])[O:8][C:5]1[CH:4]=[CH:3][C:2]([I:22])=[CH:7][N:6]=1

Participants

7

Reactant 4

HCID 807IodineHCID 25517Ammonium ChlorideHCID 55139361HCID 55139361, compoundHCID 178418918HCID 178418918, compound

Product 1

HCID 71236679HCID 71236679, compoundYield 99.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of 5-bromo-2-(3,4-difluorophenoxy)pyridine (19 g, 66.4 mmol) in tetrahydrofuran (THF) (200 mL) was added isopropylmagnesium chloride (66.4 mL, 66.4 mmol). The reaction mixture was stirred at 20° C. for 2 hr, and then I2 (16.86 g, 66.4 mmol) was added, The reaction mixture was stirred at 20° C. for another 4 hr, then saturated aqueous NH4Cl solution (200 ml) and EtOAc (200 ml) were added, the organic layer was separated, and concentrated under reduced pressure. The crude product was purified by silica gel chromatography eluting with Hex/EtOAc (20:1). The collected fractions provided 2-(3,4-difluorophenoxy)-5-iodopyridine (22 g, 61.7%).

Workup

  1. stirringThe reaction mixture was stirred at 20° C. for another 4 hr
  2. customthe organic layer was separated
  3. concentrationconcentrated under reduced pressure
  4. customThe crude product was purified by silica gel chromatography
  5. washeluting with Hex/EtOAc (20:1)

Sources & evidence

ORD record
ord-575a4cb8626443a0990ebaf5226fafbd
Source dataset
uspto-grants-2016_03
Patent number
US09273054B2

Reaction notes

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