Triacetoxyperiodinane → 1-(5-Bromothiophen-2-yl)-2,2,2-trifluoroethan-1-one

HRID 1715348Notes

Reaction equation

HRID 1715348 reaction equation
[Br:1][C:2]1[S:6][C:5]([CH:7]([OH:12])[C:8]([F:11])([F:10])[F:9])=[CH:4][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[S:6][C:5]([C:7](=[O:12])[C:8]([F:9])([F:10])[F:11])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 199715801-(5-Bromothiophen-2-yl)-2,2,2-trifluoroethanol

Product 1

HCID 199715871-(5-Bromothiophen-2-yl)-2,2,2-trifluoroethan-1-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of the alcohol (C1) in DCM at RT was added Dess-Martin reagent (1.0 eq) and the reaction mixture was stirred 3 hr and then quenched by pouring into saturated aqueous NaHCO3 solution containing 7 fold excess of Na2S2O3. The mixture is stirred for 30 min and then the layers were separated and the organic layer was washed with water, brine and dried (Na2SO4). Evaporation of the solvent gave the crude product which was purified flash column chromatography using 1-10% EtOAc/Petroleum ether to yield the desired compound as an oil. 1H NMR (300 MHz, CDCl3, 300K) δ 7.70 (1H, m), 7.21 (1H, d, J=4.2 Hz).

Workup

  1. customquenched
  2. additionby pouring into saturated aqueous NaHCO3 solution
  3. additioncontaining 7 fold excess of Na2S2O3
  4. stirringThe mixture is stirred for 30 min
  5. customthe layers were separated
  6. washthe organic layer was washed with water, brine
  7. dry with materialdried (Na2SO4)
  8. customEvaporation of the solvent
  9. customgave the crude product which
  10. customwas purified flash column chromatography

Sources & evidence

ORD record
ord-2d280ac475304ecf810c520272f46d76
Source dataset
uspto-grants-2010_09
Patent number
US07799825B2

Reaction notes

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