2-Iodoxybenzoic acid → 1-(2-Bromo-5-fluoropyridin-4-yl)ethan-1-one

HRID 1022222Notes

Reaction equation

HRID 1022222 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH:8]([OH:10])[CH3:9])[C:5]([F:11])=[CH:4][N:3]=1.I(C1C=CC=CC=1C(O)=O)(=O)=O>C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[C:6]([C:8](=[O:10])[CH3:9])[C:5]([F:11])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 1087942-Iodoxybenzoic acidHCID 75480808HCID 75480808, compound

Product 1

HCID 252229461-(2-Bromo-5-fluoropyridin-4-yl)ethan-1-oneYield 92%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 325b (7.5 g, 34.2 mmol) and 2-iodoxybenzoic acid (38.4 g, 137 mmol) in ethyl acetate (200 mL) was stirred at 85° C. for 20 hrs. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica-gel column chromatography eluting with petroleum ether/ethyl acetate (20:1 to 10:1) to afford 325c (6.8 g, 92%) as a yellow oil. MS-ESI: [M+H]+ 217.9.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe resulting residue was purified by silica-gel column chromatography
  4. washeluting with petroleum ether/ethyl acetate (20:1 to 10:1)

Sources & evidence

ORD record
ord-6d5e1021797d4195b094f601951ab699
Source dataset
uspto-grants-2014_05
Patent number
US08716274B2

Reaction notes

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