Triacetoxyperiodinane → 1-(4-Bromopyridin-2-yl)ethan-1-one

HRID 879574Notes

Reaction equation

HRID 879574 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH:8]([OH:10])[CH3:9])[CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8](=[O:10])[CH3:9])[CH:3]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 847213964-Bromo-2-(1-hydroxyethyl)pyridine

Product 1

HCID 234370521-(4-Bromopyridin-2-yl)ethan-1-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of 1-(4-bromopyridin-2-yl)ethanol (2.93 g, 14.5 mmol) in DCM (50 mL) was added Dess-Martin periodinane (12.93 g, 30.5 mmol) portion-wise over several minutes. The reaction was then quenched with saturated 1:1 Na2S2O3/NaHCO3 solution (200 mL) and stirred until gas evolution ceased. The aqueous layer was extracted with DCM, dried over MgSO4, and purified by column chromatography (gradient 0 to 10% EtOAc in hexanes) to give the product. 1H NMR (400 MHz, CDCl3) δ 8.50 (d, J=5.2 Hz, 1H), 8.20 (d, J=1.9 Hz, 1H), 7.64 (dd, J=5.2, 1.9 Hz, 1H), 2.71 (s, 3H).

Workup

  1. customThe reaction was then quenched with saturated 1:1 Na2S2O3/NaHCO3 solution (200 mL)
  2. extractionThe aqueous layer was extracted with DCM
  3. dry with materialdried over MgSO4
  4. custompurified by column chromatography (gradient 0 to 10% EtOAc in hexanes)
  5. customto give the product

Sources & evidence

ORD record
ord-68b42f2e4d0d41a5b792c058d3ce98e3
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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